3-Amino-2-isopropyl-4-oxo-2,3,4,5-tetrahydro-1,5-benzothiazepine-5-acetamide → 2-Isopropyl 3-(2-indolecarboxamido)-4-oxo-2,3,4,5-tetrahydro-1,5-benzothiazepine-5 acetamide

HRID 345146Notes

Reaction equation

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

Participants

Conditions

Temperature: 70 °C

Procedure

A solution of 1 g of 3-amino-2-isopropyl-4-oxo-2,3,4,5-tetrahydro-1,5-benzothiazepine-5-acetamide and 1 g of succinimido 2-indolecarboxylate in 35 ml of dimethylformamide is stirred with heating at 70° C. Twenty-four hours later, the reaction mixture is concentrated under reduced pressure, whereto 50 ml of saturated sodium hydrogencarbonate and 50 ml of ethyl acetate are added. The mixture is stirred for a while. The resulting crystals are collected by filtration and recrystallized from a mixed solvent of dimethylformamidemethanol to give 0.92 g of 2-isopropyl 3-(2-indolecarboxamido)-4-oxo-2,3,4,5-tetrahydro-1,5-benzothiazepine-5 acetamide, the decomposition temperature being not less than 300° C.

Workup

concentrationTwenty-four hours later, the reaction mixture is concentrated under reduced pressure, whereto 50 ml of saturated sodium hydrogencarbonate and 50 ml of ethyl acetate
additionare added
filtrationThe resulting crystals are collected by filtration
customrecrystallized from a mixed solvent of dimethylformamidemethanol

Sources & evidence

ORD record: ord-7a22db2118654c028931e2e62410daae
Source dataset: uspto-grants-1991_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05055464

Reaction notes

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