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AES AILV 107 LOBHY Be) AY (METHOD PORPREPARATION OF GAMMA-AMINO-BETA~PHENYLBUTIRIC ACID HYDROGEN CHLORIDED Sr 24 J 25 EME fi BSE 1 AS Ae NATTA EA AA RE BL RL BI: EAT BAL he «A LA SF WE Dg BU 28 5 TS RZ CES PSA FB Di» PS BARING Fi LS BV AA A 5 5 LS RE I 2 TZ AR 5 RIDE I » 2 0 AS ML UE A IE 2 BH ATT FA ALR AR A RS EE UT AR RPA [£0004] Fh AS FRAG CNL 0235 1 726/85 2) Ae FUL IP EL SALAS SO i HT] AA HAE YATE WARY SAB Ey SSR 2 AT IG EG SE GD» ZACH» TE PEK WA BAAR «HE GBA IR) SOE SL) He TA 2 I 5 IT GAS RAL EE PA FAR BC A BAR CR AIC IR (0005) FAN: 5 WE BFE Bt — A 5 SA Rh GL A Ge 5 MED ER BE EAS I NM SIRE RAGES HTM A AAS iS eT TE BAAS Coos] 4s Az wy Ely AEP Sab UL ie il AS «Dy LB RPA LS IM RPE SA 5 I NC Be A EG SBT A [0007] Fy SEEMED ELD » AS ARB ALE A ASI Rs — A a Hp TEE, FPR Coos] (1) PEAY LHR STUT 5 ZERRAE LEE 5 1 PUT ATH A) He Wee Bs TS I FF AF SL, ASSIGN Pras 4 TAE-3 RIE T ARLEN» Ne THe TR ON. SS [0009] Ba ORCN 106083685 4 hh A 2/9 Fi Cooro] 3th SCL ANS Dera Ruite AI CL-Coni Beas Coort] (2) ep Lie AHH, FUG DR PAE RR LL a 4 E-BAY eG NY IE Jes SRILA 9 B42 Coor2] (3) 4E 77 BLAU ATR RT TTB astY oe Z. a AE 42 1B S498 2 IRAE AT EAE A PBA V AR tA SEO HEH 1—-ZL AE » Ph (0013) ° | OR RyHC—C—o0—R, ° utr WV Coorg) $kefs SULT LAUER LVAD Rede A C1L-COM yee SUL LH AIR Sa HR Coors) (4) AEA LIRE TAN LV IIE as) 4-8 SEU AB —1—Z, Re EG Gk EAT BL FSB FR EL i BIA Coote) CEPA CL )— (4) He IPRA UL ARE AUS a ea Hoe» BES SS PA IN N= = FSi FF BB ge SN, N——2 FRAG ZAC SN, N— 2 FU GO Ls FS RS FACIL —CAH TE PITA 19 AG AZ. PRS Ue PIR PR eae RU ie PE (3) 6 JAAR ES 4 LFA La FIN, N——. FRE FEN N— 2 FFE ZV SLR, SRF HS ISA PAL FE Rite Sak AVE 2 A AV EER Z, AG A PER ATS AV HERTS ALE 2 OQ PHA SP PAS AEE eT 9 — BLA PPAR OZ, PIE A A SZ HA LZ, PRL SUZ RP SZ RT RZ SZ PT SZ BZ. 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BK (DIA). ‘t-BuOK CHlsONa \CHs0K \CllgCHsONa \CHaCHLOK "} 4) FBR LPH s ZETA (2) TR AER, FASE BR ART LOR sO) AWE —3— ARE TP AE A WW A ACE BE: CCIE: Be FRE GN A HO) — Bs PT 0 A a HE SRF MN AC NAIA A 2a SAC FITS BN PE DRG KE Ig BN LAA ok SCAR: RBI A BESE—3— AE TOR ZAK Ae SL RARE 1-5, iRSEG EFI PEAR HE 9 1 1-2: 3-5 » BEAM PR ARG IY: 1-225 PTE 3A AE TPZ A SAAT LAE SRE AAR Jes» SE EB RN I ANI PSA RAT A SA» FEAT PEST SBE Bg OM 5 FOES Fe ah FETS SED MAAN Io SA SL AA BE 20 OC, FIERA TASS SiC I IER HL E050 °C RRA ITA UT HH BAIA REA 20-30°C 3 ZE PrrSeR AE CL), BAR OF AD Ee 98 3 AP eR ARG Ls 1-52 1-5, EAN AR SLs 1:1 s ARSAR HMR I 1 4 BG ML BE 90-50 CHR BR MME HE 920-30'C 5 PET EH HRC 3) 5N_ 106083685 hh A 39K of PTR A 3 UCU AGB a] ZG EIN IT ME AS Hg 1 5 15» HAE AR ELL: 222 FARA AA ARE 2-H sc ak ZR eA DS MF 9 A 2 BH FACIE 3 ANY PRIA NLO—3 INI 5 FDA ZL, PR SS » Sh 9 FZ NE L—3 IND, Rid Sk se E23 lM 5 A FITS TT ZR EE AS 1 LE 9-20~O°C A Fara UDG Ze Ae HW J SOR 2S FN PBS Q-10~ 30°C TMA Fa aS RA GZ, BR oe J a BES SLES HA FSE A910 ~0'C 5 ZETA A RCA), PAR A LG ae TDR IL s OTSA SA BE « TS HEAT BE BE V0—-40°C: Ubi NE 20-30°C « (0017) AS Ae AE BE a EP — a AS AO SEL ap HH RR C1) TE AIRE AT AEH LIRA LUPE BRE BEE 0 (2) ALR OY TAS RIE IIE BEAR TR SEG LACIE 5 Be AR LI» AT SET ME A 0 (3) ZRF hh IME $i SEL EPL CH A RALIOWLA Leo Coors) — ia Mt i SEL fl A Pa Bd: SILAS AR» BE RA SEINE ER RAE SEAS I INC BE as HP REZ A TA 2 PAELLA Coors] “Faiz APA Pale Se HAL Ry AS AR EAT EAE. (0020) FAL AEA A OH ti ee RL AKTHAR Cot] LED 2eh 2 SK A wet As a Bk — 2 BA» SI AF ET ee A 9 5 EL ABH IE AMAL ABET TRS Hs (0022) Se jis] — [0023] 4- FA AE-3—AE MET RZ, A Hl A (0024) (1) REFER ASLAN ASIA] BR A Ee fl INE BO (0025) fay FALE DMA 200mL FE 7k FE» PL HERR ZA WEE AP se O° DAE Se a HM 9 30.6 NaOHAR F584 » FUT RBIS AST AR AR EL PE ik PATE LAE L, 20-30°C JQ BED , 9 BE PBL ESC ERT 40-50°C PUG HRA AS HH FH SLAPS FAL» NL OOm | 7K.» 5} 54) FL SOm — SFP EE A ARIK, SIF RES, 40m) NER MEHR Ue FE D4 Om Lk eR — a 7 BT A RSD A UAE REP IM A Big FE ZA THER BE TPR Oh Jt LE RE AS A AEA PS BUTE Bh, WDA ME-3 SRE TAR, 5 Pat CHIE ML EL (0026) a1: IISA) AST AR ARE (PPTL RAW IE-3— RIE T PZ, MU FS aECN 106083685 4 hh A 49K Fe | VEER CRE. TEESE, BRAUER RAR HG | PEE | RAR UCR = fi) g % 17.6 g (0.1 mol), 6.1g(0.1 mol), 4gNaOH 1 (0.1mmol) 16.6 70 Ll 17.6 g (0.1 mol), 12.2g(0.2mol), 8gNaOH tor) | 2 (0.2mmol) 15.4 65 132 17.6 g (0.1 mol), 6.1g(0.1mol), 8gNaOH 3 (0.2mmol) 154 65 11:2 17.6 g (0.1 mol). 12.2g(0.2mol), 4gNaOH 4 (0.1mmol) 149 6 12:1 (ooze) (2) AA AST fr 5 MUR FEY Nase 3 8 Os (looz9] fa] = FHL ANA 200mL FE 7k BE 176g (0. 1mol ) PY FERRZ. BH 6. 1¢(0. Imo ) A 3E FR °C DAF SEES i 10 . Sm. 79 £4930 % NaOH (0. Lmol ) AK HRB (4gNaOH/9. 5gllo0) FER JBI A #3 BQ WMEIDR » FITS — ed EA AG PAUSE IL B82 AE BEI 40-50 CF CR HAR HPL GES FIL OOmI 2K 5 Sl] FES Om] SR HEE A ANN U5 Ao HE SA oe AL OmL IN RMI UC HELA Om A GBR UA Js PY A HBL s FLA PIA BF A TE PREP L—2h Je ETE RG AS HH HG i FUE BE STH A 3A TR PR NTE LAR: C0030] SE BE APT Be AT ET REZ Bai Be Sc [0031] FES SSH BEC Be BRAKE % 1 10-20 15.6 66 2 20-30 16.6 70 3 30-40 15.4 65, 4 40-50 14.2 60, Loose] (3) ARAL AST Ay Bik xt i Bie FN BY (0033) fay = 01 LH A 200m Erk FAY, 17 -6g(0. 1mol ) ASEERRZ. Ri -6.1g(0. Lmol a3 FRG °C DAF EADIE D4 (9 BARI BE, 20-30°C INE 2h, FEB INE HE FTA RA HAR POL LS SHERMER T 40-50°C BFR He AR HF LTE DN LOOM 7. 3 Fi) AL8Om | SAP SEHR A RPK, OFF SUP EAE FAOm1 INRRAR ERR UK FE AL 40m1 7k Bee Ue ee 4 BT BLA FRSBLs A UUARPE REP UA 8 FEZ THER ER TIE LO Ft MER FS TEE PB BE Se, WD4—WISE—3—8 HET AR 5 Pat ENE ML RES (0034) 83 BRIA PEER Bed TRS 3— AEE TR, aN 7a SCCN 106083685 4 hh A 5/9 Fi ES Bi Ae [me 1 NaOH 16.6 70 2 Na,CO3; 15.4 65 [0035] 18-2 RRB RT 3 ak 142 60 4 PU EAM 15.4 65 =ZIk 145 61 (loose) Se iti |= (0037) 4-92 —g bc a Coosa) (1) EAA AST (es BAT Hd: wt NN [0039] 4 FE —3 FEET ABZ. AHL . 6g. 07 mo] ) FAJ250mL — SUF be FAA BH BE Hk 8 — 10°C SELINA O 35m 15 AFA AMEE | FFE 15-30 °C HBR WES 5 FEB ME IPS HAE PRA DE ML-ZE 5 HR WLR EAE 40°C, INA 55OmL 10% Ai HM» 55OmL — 48 HE 20-30 “CHEROKEE AED BY, UB e9OmL x 2AEAL rk ak Ao IE RP Ase aE 120% SAA, 7K ME220ML x. A BLATRERBL MA 8:76 7k BAR BEER L-2h Jia RENE FR AR SREP A 5 FSS AR BE il fF 2 5 FE EGE LE (004) a1 ASG AY ae PRAISE DAR EO SN SE [0041] IEA PERL g | RARE BACAR A CE y AONE TRE) os (0042) 2 BB 19 70 3 TEMANOE 9.3 82 4 ALA 9.0 80 (o04s] (2) ARF ISLAY ASAI BE A He ol De RE SF (lo044] 4-H 3—IR IT RZ. Bl FE 25OmL — SP sae HE BA B—10°C AK A SCAR PERE 8 - 10°C, Sh dt HE AA» DE, Ft; B15 30°C HINA RAMESH ABA) 5 SERBE , FATS SH(19 AS TE AS Ee LL Sa PAPE DW 2 2 HF PEE Ah EOC, MAB 5OML 1096 ARERR» 550mL UF fe 20-30°C HAE A HEI TP FERN TY FP OOM. x ZALES» Fre SUP HEEL» F120. SA ANA He LZ x APLAR EP IMA Se FEA BER SEP HR I-2h UE aR 2 Pt — SL A 5 FSA BE ET ed — ARIEL AC» Hk Be 3 TE WAR (0045) e2: WGA ASTRA AE AE SRR IL AE 2 AS 7 BSCN 106083685 4 hh A 6/9 Fi e 3A TRCN. NKR. | EEE | MEARE a AACA IRY EA IRE AR Ea g % 16.6 9(0.07 mol), 16.6 9(0.07 mol), 13.2 (0.35 1 mol) 96 85 Lbs Co046] 16.6 g (0.07 mol), 16.6 (0.07 mol), 7.9 (0.21 2 mol) 9.2 81 1:13, 16.6 g(0.07mol), 33.2 9(0.14mol). 13.2 9(0.35 3 mol) 9.6 85 1:2:5 [0047] (3) A ANTD RY IQ RACHA EA i 9 BA (lo048] pA HY SE-3-FEIE TAZ. BG 16.6 g(0.O7mol ) FI250mL — SUF AEM, — HEHE BE PEINALG.6g( 0.07 mol AAR A SUL ANS HEAM A 13 . 2 (0. 35mo 1 ) HEAL AN HE Ft ELS 30°C HEINP HH Qh» 4 BY SNAPE FIT AS Fe aL PEF SEA A PEAR LZ AE LIME ML EOC , INAS 50m 1026 i th -550mL — RAE, 20-30 °C HEE RRR FUN AY, ALFA oe 9O0mL. x AIA 5 EUR SEIS » FL 20.% SUA BN BE 220mL X 33 SUK 1 A BALE RL MN AB FEA THEA BP RL 2h is EE I AR Bie UK BT (SE — 2 Be» PR DUE LES (0049) Ak Fi AUREL RENN HALPER, AS 2 mL So 7 UNC : EME FEA, a PS | “imtaearremeeiaee | AEs | Asti {0050} 1 -10-0, 20-30 9.6. 85. 2 -20~-10. 20~30 9.6 85 3 -10~0, 10~20 19 70 4 -10~0, 40~50 73 65 (00st) Seif |= (0052) 4-295 E—2— AG B12. FA Hd C003] (1) RAY AST AP LIA FRE ie NC 1 [0054] AAI —2-WLM EAD 6g (0. O6mo] )38E-F LOOmL Ag ALE HU ITA AL Le a a PRN UL NLAE1 , BEA 8 A A-10°C AE, SP MAIS. 5g (0. 12mo1 ART EA ME F-10—0 “CARSEAT 2h , BEIEL 48 ATEL-10°C FRE HMI3.0g (0. 12mo] ) KZ. EF AK. F-10—0°C HEE Be hie AUR, MA LGOmL Z, ABZ, Be 6SmL ANCHE P/O SmL.K HEA HE BLS} fas 7K SOL x 2ZARZAGR LK, TIE AT ALES PAUL Hed OmL X 22K. AOMLAK BEL 8g FE ATH IR EE PRBOmin LIE FITS EE TARA , BAA E21 SL ~ ZF» FP UT ae (O55) Be 2 4a AL FEE HUH HAG EA OE B42 AB 1-Z, PR A FGCN 106083685 4 hh A U9 oo TER AULA FEE g | PEARY L N,N- FEF A COME) 17 84 2 NN HSE Z, EH ILS 82 [00571 4 eI 10.9 78 4 SURGE 9.0 64 (loos) (2) EFL ASIA) BR A LE fol Fe Ne A 0059] ESE~2-HE MERA T10OmL DMEHH BEEZ AV IL-1O°C BEA, SPC ACT EH RT —10—0 CARSEEAE ON , BE HEL 28 A A-10°C , APIS, FP FT SE AS FRU BUA SBP LIL 22 s F—LO—0 C REE BLL HELA FNAL 6OmL.Z, RZ BS OSL Af FURL He /OSmL AK APH LS AK 8 OmL x 22, RZ ARK, IATA LL, PGAOML X 22K, AOmL ABEL , BALAK HEB ET ARO n LAE IIE AE EMD » BE FL-2 ALM AEH —Z, BRP 7S Ea EH TL WLR (0060) 82 BRE ASIF RA LU UN PAG DAA 2 1 ~Z, A NE VY | 42 SE-2-uie sel, CARTE. CT RR | pat | WEAR = BRL IRs EC g % 9.6 g (0.06 mol). 13.0 g(0.12 mol), 13.5 (0.12 i mol) 17 | 84 1:2:2 C0061] 9.6 g (0.06 mol), 32.4 g(0.30 mol), 33.7 g(0.30 2 mol) 109 | 78 15:5 9.6 ¢ (0.06 mol), 6.5 g(0.06 mol), 6.7 (0.06 3 mol) 2) 80 Ltd [0062] (3) AR PAL AS Ta 19 a A ALTE ASL, SIRE CSS — i ) A IE PE SS HLFEE) te NC RS (0063) HAAR I-21 GBH 6g (0.06mo1 HEF LOOmL DME Se FSi FE tC DN AA3.5g(0. 12moL ALT BE In HE TS — a Bk EEE Be 22h PEA 8 ALL 10°C , TB iE BET IN 13.09 (0. 12mo ) 582. FRFF HG, T-3 —iek BE AS: 5 Lh, FITS SE Ak SEAS — HOSEA DL ML AES MTSE, MA L6OmLZ, 12 Z, HS» OSL HB ANAL AL Be /O mL A HE SP Je IK ERU8OML X 2Z, FBZ ALIKE AT BLS» HOA RAL BR AOML, x 2ELIK » AOmLAKGEL HR BaF A THAR FAR 3O0min LE RE AR » REA BLUES (oe) eh YEA SE ASS 3k PSEA a PAIL Dd HOA 7 [0065] FS DWE RO BEC fife FRAICHE IG 1 =10~0,-10~0 17 84CN 106083685 4 hh A 8/9 Fi 2 =20~=10,-10~0 12 80 3 =10~0,0~10 10.5 5 4 =10~0,10-20 8.8 63 5 =10~0,20-30 8.4 60 Coase) (4) ARAL AS Ta fy BQ SY Te ig SC BV (0067) 4-9 IE- 2-1 EBD 6g (0.06mo1)##-F100mL DMPH? , ha 38 AL IL-10°C dE SPUIMA 13. 5g (0. 12m01 ART BEA HET —5—0 °C BREA J OE — 5 ET , Ba 28 10°C FF NL3.0g(0. 1 2mo 1 ) SZ, HEF AG. FB —0°C Sk 2S Je BL — SINS TFT AS se MEO Ti PENT UL ULBEA ; SZ MEAG MAL 6OmLZ, EZ. AS 5 6SmL ALLAN SAL He /65mL AK SESE FL SP Dat AC FESHSOmL x 22, FBZ. HEALD 5 A HE BLISS» UAL RAG He AOmL X 232 40m AACE LIK 8 FE TR TR EFS 3Om i 5 LTE 5 FEB CAR, BASE 2 We GS BE PTR LS 4s (oo) eas Fc ARAN Ti] HAG TE 2 AAR EDL Ho NC IMA ART 8H TA 52 BEIT TA), eS MASCARA BEMIS | EE ge | RAR % reel fal, est 1 Ld 10.9 78 2 2.2 7 84 3 1,2 112 80 Ae 4 21 112 80 3 3.3 117 84 COO71] (5) RAY AST ei Z. Pac AE a Ie A TS (0072) AAR I-21 EBD 6g (0 .06mo1)#-F 100ml DMEF? , ah 38 PLIL-10°C dE PUINAL.5g (0. L2mol ALT AEH, IHEP —5—O'C ABE EE 2h, BEAL 2 PY L- 10°C, DN (0.1 2mo1 ) ii ZR » AS ei Z, RR Da PAAR SLES s P—-5—O'C ARE BENE Bh BEA IMALGOmL. 2, FZ, A » GSmL AU SUL He / OSmL AK ABA PLY Hee AK Fe 8 OmL. x 22, 8 Z, RAE WRK, HEAD LAN SUL He AOmL X 2BEQUK AOML AA BELEK Be FE 7k TRA RFR 30min , i WE AIRE CS MR WD E25 FEU RAG TR MLE (0073) 85 pal Z, MARA LAGER INE Be RE 2 re 7 BSC on ait) RAK FPR | ZN : | as 1 SACRA 1L7 | 84 eae ae ALL 16 | 83 3 ALBAN 1s 8 4 RCT Th | 3 (oo7s] Se iti) (loo7e) Asi dy DSA filCN 106083685 4 hh A 9/9 Fi Coo77] (1) ARAL AS TA Ar LAE ae [0078] F11.7¢(0.05mol )4— AE 2-H rk 1— Z, AF M4 BS AE 5OOmL ALR BME 5 SA 250m 38 FA) FAS FE A SEE IAL EL HAY SAIYAN, 20-30°C OME Zh AT FPR DSLR BCH, SYS AO CLI RHE FALE FESTA «IAA Om EAT 2 AC EAH PASS SAU EDTA TTR LA» ST ASB CED PSO EL ZA SEAT MAL C0079] eds Fi ML SRE SIN ia PRIN. 21-8 EOL So 1—Z, POE PB [0080] RS AALS FA ie FEAR 1 ae 8.8 81 2 Ze 8.5 78 3 FEE 7.6 70 Coot) (2) AA AST fy RHA IE AT NN [0082] $11.7 ¢(0..05mo] )4— AR AE—2—ME Me AEH —Z. HR Ae BS 3B 5 0OmL Me FR EH IMA 250m FFA EA LA 5 ESB — FE RE FFB PR TES 3b PE TIE LEZ, 20-30°C FE 12h FT FE IRIE HALE HACE BU» SEACH 2 SS RE 8 CHL ELE 5 TL A Om HE 48 IE OLAS UL AL 5 Fe PE A 9 2) aT 28 3-2 Soe 1 — Zk LL 2: (003) a2 GUAR SEA TAREE ARIE 2 MLN Bre, OE LEAN Fd EG (0084) FES BUNSIR IE fe FEARU EG I 5 49 5 2 Seta Tl 65, 3 a 8.8 81 0085] (3) AAAI ASTD AY IQ RUHL HE a Die INE 2 BZ (0086) R11. 7¢(0.O5mo 1 4-2 8 —2-MLNA Ae HII —Z. 2 AGS SAE SOOmL eh HE SMA 250m 22. FY HED AIL) 5 — 9 ULE JQ EL hn TSAR — HIE 2s PR LOS AT FP HALEN» ACH AU SVE °C InP 2 FE 8 ACHP EA DNL OLB BS EF SE MY» PS HA 4 8 8 4— 8 I-21 ZK 5 FH ML: (ooe7] 63 2 NEAL EH HAGA OL Ba A -AE—2 ML ~~ Z, POL 4B [0088] ie FS SUSHI IEC ithe BEARISH 1 0-10 7.2 66 2 10-20 8.3 76 3 20-30 8.8 81 4 30-40 7.0 64 (loos) AIH RIG CL ~ CO ESE RII ACL ~ COND ESE ROME A I BLLCN 106083685 4 he Bt LAK on. CNOs Nid. NaBH eee oo : on ae