(3aR*,10aS*)-9-[4-(benzyloxycarbonylamino)benzyl]-4-(phthalimidoacetyl)-2,3,3a,4,9,10a-hexahydrobenzo[b]cyclopenta[e][1,4]diazepin-10(1H)-one → (3aR*,10aS*)-9-(4-Aminobenzyl)-4-(phthalimidoacetyl)-2,3,3a,4,9,10a-hexahydrobenzo[b]cyclopenta[e]-[1,4]diazepin-10(1H)-one hydrobromide

HRID 361571노트

반응식

HRID 361571 반응식
C(OC([NH:11][C:12]1[CH:47]=[CH:46][C:15]([CH2:16][N:17]2[C:23](=[O:24])[C@H:22]3[CH2:25][CH2:26][CH2:27][C@H:21]3[N:20]([C:28](=[O:41])[CH2:29][N:30]3[C:34](=[O:35])[C:33]4=[CH:36][CH:37]=[CH:38][CH:39]=[C:32]4[C:31]3=[O:40])[C:19]3[CH:42]=[CH:43][CH:44]=[CH:45][C:18]2=3)=[CH:14][CH:13]=1)=O)C1C=CC=CC=1.[BrH:48].C(O)(=O)C>C(Cl)(Cl)Cl>[BrH:48].[NH2:11][C:12]1[CH:13]=[CH:14][C:15]([CH2:16][N:17]2[C:23](=[O:24])[C@H:22]3[CH2:25][CH2:26][CH2:27][C@H:21]3[N:20]([C:28](=[O:41])[CH2:29][N:30]3[C:31](=[O:40])[C:32]4=[CH:39][CH:38]=[CH:37][CH:36]=[C:33]4[C:34]3=[O:35])[C:19]3[CH:42]=[CH:43][CH:44]=[CH:45][C:18]2=3)=[CH:46][CH:47]=1

참가 물질

4

반응물 2

HCID 15385743(3aR*,10aS*)-9-[4-(benzyloxycarbonylamino)benzyl]-4-(phthalimidoacetyl)-2,3,3a,4,9,10a-hexahydrobenzo[b]cyclopenta[e][1,4]diazepin-10(1H)-oneHCID 21893785Acetic Acid Mixture with Hydrobromic Acid

생성물 1

HCID 67767990(3aR*,10aS*)-9-(4-Aminobenzyl)-4-(phthalimidoacetyl)-2,3,3a,4,9,10a-hexahydrobenzo[b]cyclopenta[e]-[1,4]diazepin-10(1H)-one hydrobromide

시약·촉매·용매 1

HCID 6212Chloroform용매

실험 절차

To a solution of (3aR*,10aS*)-9-[4-(benzyloxycarbonylamino)benzyl]-4-(phthalimidoacetyl)-2,3,3a,4,9,10a-hexahydrobenzo[b]cyclopenta[e][1,4]diazepin-10(1H)-one (5.15 g, 8.2 mmol) in chloroform (80 mL) was added 25% hydrogen bromide/acetic acid (15 mL) and the mixture was stirred at room temperature for 45 minutes. This reaction mixture was concentrated under reduced pressure and the residue was crystallized from ethanol-diethyl ether to provide (3aR*,10aS*)-9-(4-aminobenzyl)-4-(phthalimidoacetyl)-2,3,3a,4,9,10a-hexahydrobenzo[b]cyclopenta[e][l,4]diazepin-10(1H)-one hydrobromide. This product was suspended in chloroform and treated with 0.5N-aqueous NaOH solution (40 mL). The aqueous layer was separated and the organic layer was washed with water, dried over MgSO4, filtered, and concentrated under reduced pressure. The residue was crystallized from chloroform-diethyl ether to provide 3.71 g (yield 91%) of the title compound. m.p. 286°-289° C.

후처리

  1. concentrationThis reaction mixture was concentrated under reduced pressure
  2. customthe residue was crystallized from ethanol-diethyl ether

출처 및 근거

ORD 기록
ord-1b897231e5e04c8387e7e634fce8a4b4
출처 데이터셋
uspto-grants-1999_02
특허 번호
US05866567

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