(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 361571ノート

反応式

HRID 361571 の反応式
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

参加物

4

反応物 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

生成物 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

試薬・触媒・溶媒 1

HCID 6212Chloroform溶媒

実験手順

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.

後処理

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

出典と根拠

ORDレコード
ord-1b897231e5e04c8387e7e634fce8a4b4
出典データセット
uspto-grants-1999_02
特許番号
US05866567

反応ノート

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