Anisole → trans-3-(2-Indolecarboxamido)-4-oxo-2-phenyl-2,3,4,5-tetrahydro-1,5-benzothiazepine-5-acetic acid

HRID 345155Notes

Reaction equation

HRID 345155 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[C:2]1[C:10]([NH:12][C@@H:13]1[C:19](=[O:20])[N:18]([CH2:21][C:22]([O:24]C(C)(C)C)=[O:23])[C:17]2[CH:29]=[CH:30][CH:31]=[CH:32][C:16]=2[S:15][C@H:14]1[C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)=[O:11].C1(OC)C=CC=CC=1.Br.C(O)(=O)C>C(O)(=O)C>[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[C:2]1[C:10]([NH:12][C@@H:13]1[C:19](=[O:20])[N:18]([CH2:21][C:22]([OH:24])=[O:23])[C:17]2[CH:29]=[CH:30][CH:31]=[CH:32][C:16]=2[S:15][C@H:14]1[C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)=[O:11]

Participants

5

Reactant 3

HCID 7519AnisoleHCID 14648565Tert-butyl trans-3-(2-indolecarboxamido)-4-oxo-2-phenyl-2,3,4,5-tetrahydro-1,5-benzothiazepine-5-acetateHCID 21893785Acetic Acid Mixture with Hydrobromic Acid

Product 1

HCID 14648568trans-3-(2-Indolecarboxamido)-4-oxo-2-phenyl-2,3,4,5-tetrahydro-1,5-benzothiazepine-5-acetic acidYield 78.3%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

While a mixture of 5 g of tert-butyl trans-3-(2-indolecarboxamido)-4-oxo-2-phenyl-2,3,4,5-tetrahydro-1,5-benzothiazepine-5-acetate, 15 ml of acetic acid and 2 ml of anisole is stirred at room temperature, 21 ml of a 30% solution of hydrobromic acid-acetic acid is added to the mixture dropwise. After the mixture is stirred at room temperature for 9 hours, the resulting crystals are collected by filtration and washed with ethyl acetate to give 3.5 g of trans-3-(2-indolecarboxamido)- 4-oxo-2-phenyl-2,3,4,5-tetrahydro-1,5-benzothiazepine-5-acetic acid, m.p. 260°-270° C. (decomposition).

Workup

  1. stirringAfter the mixture is stirred at room temperature for 9 hours
  2. filtrationthe resulting crystals are collected by filtration
  3. washwashed with ethyl acetate

Sources & evidence

ORD record
ord-0a4e46412b9045efb6377a74dcc50121
Source dataset
uspto-grants-1991_10
Patent number
US05055464

Reaction notes

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