Ammonia → trans-3-Amino-4-oxo-2-phenyl-2,3,4,5-tetrahydro-1,5-benzothiazepine-5-acetamide

HRID 345143Notes

Reaction equation

HRID 345143 reaction equation
[NH2:1][C@@H:2]1[C:8](=[O:9])[N:7]([CH2:10][C:11]([O:13]CC)=O)[C:6]2[CH:16]=[CH:17][CH:18]=[CH:19][C:5]=2[S:4][C@H:3]1[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.[NH3:26]>CO>[NH2:1][C@@H:2]1[C:8](=[O:9])[N:7]([CH2:10][C:11]([NH2:26])=[O:13])[C:6]2[CH:16]=[CH:17][CH:18]=[CH:19][C:5]=2[S:4][C@H:3]1[C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1

Participants

4

Reactant 2

HCID 222AmmoniaHCID 14648534Ethyl trans-3-amino-4-oxo-2-phenyl-2,3,4,5-tetrahydro-1,5-benzothiazepine-5-acetate

Product 1

HCID 14648538trans-3-Amino-4-oxo-2-phenyl-2,3,4,5-tetrahydro-1,5-benzothiazepine-5-acetamide

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

In 600 ml of methanol is dissolved 20 g of ethyl trans-3-amino-4-oxo-2-phenyl-2,3,4,5-tetrahydro-1,5-benzothiazepine-5-acetate, into which ammonia gas is blown to the level of saturation under ice-cooling. The reaction temperature is slowly elevated to room temperature, and the mixture is allowed to stand still for 24 hours. Then, the reaction mixture is concentrated under reduced pressure. By adding isopropyl alcohol to the obtained residue, crystallization is effected. The crystals are collected by filtration to give 18 g of trans-3-amino-4-oxo-2-phenyl-2,3,4,5-tetrahydro-1,5-benzothiazepine-5-acetamide, m.p. 217°-219° C.

Workup

  1. temperaturecooling
  2. customis slowly elevated to room temperature
  3. concentrationThen, the reaction mixture is concentrated under reduced pressure
  4. additionBy adding isopropyl alcohol
  5. customto the obtained residue, crystallization
  6. filtrationThe crystals are collected by filtration

Sources & evidence

ORD record
ord-6b48eddc9d5945a9b371cec852e4480b
Source dataset
uspto-grants-1991_10
Patent number
US05055464

Reaction notes

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