Tert-butyl trans-3-amino-4-oxo-2-phenyl-2,3,4,5-tetrahydro-1,5-benzothiazepine-5-acetate → Tert-butyl trans-3-(2-indolecarboxamido)-4-oxo-2-phenyl-2,3,4,5-tetrahydro-1,5-benzothiazepine-5-acetate

HRID 345154Notes

Reaction equation

[NH2:1][C@@H:2]1[C:8](=[O:9])[N:7]([CH2:10][C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[C:6]2[CH:18]=[CH:19][CH:20]=[CH:21][C:5]=2[S:4][C@H:3]1[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.[NH:28]1[C:36]2[C:31](=[CH:32][CH:33]=[CH:34][CH:35]=2)[CH:30]=[C:29]1[C:37](ON1C(=O)CCC1=O)=[O:38]>CN(C)C=O>[NH:28]1[C:36]2[C:31](=[CH:32][CH:33]=[CH:34][CH:35]=2)[CH:30]=[C:29]1[C:37]([NH:1][C@@H:2]1[C:8](=[O:9])[N:7]([CH2:10][C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[C:6]2[CH:18]=[CH:19][CH:20]=[CH:21][C:5]=2[S:4][C@H:3]1[C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1)=[O:38]

Participants

Conditions

Temperature: 60 °C

Procedure

In 300 ml of dimethylformamide are dissolved 18 g of tert-butyl trans-3-amino-4-oxo-2-phenyl-2,3,4,5-tetrahydro-1,5-benzothiazepine-5-acetate and 12 g of succinimido indolecarboxylate as synthesized by a known method, and the solution is stirred at 60° C. for 33.5 hours. The reaction mixture is poured to ice-water, and the mixture is stirred to separate crystals, which are collected by filtration and washed with water and dried to give 22 g of tert-butyl trans-3-(2-indolecarboxamido)-4-oxo-2-phenyl-2,3,4,5-tetrahydro-1,5-benzothiazepine-5-acetate, m.p. 196°-200° C. (decomposition).

Workup

customas synthesized by a known method
stirringthe mixture is stirred
customto separate crystals, which
filtrationare collected by filtration
washwashed with water
customdried

Sources & evidence

ORD record: ord-0224101d289e4d839816eb7d9ee16979
Source dataset: uspto-grants-1991_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05055464

Reaction notes

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