(2S,3S)-3-(2-aminophenylthio)-2-hydroxy-3-(4-methoxyphenyl)propionamide → 3-Hydroxy-2-(4-methoxyphenyl)-2,3-dihydro-1,5-benzothiazepin-4(5H)-one, (2S,3S)-

HRID 1457247Notes

Reaction equation

HRID 1457247 reaction equation
N[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[S:8][C@@H:9]([C:15]1[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[CH:17][CH:16]=1)[C@@H:10]([OH:14])[C:11]([NH2:13])=[O:12]>C1(C)C(C)=CC=CC=1>[OH:14][C@H:10]1[C:11](=[O:12])[NH:13][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=2[S:8][C@H:9]1[C:15]1[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[CH:17][CH:16]=1

Participants

3

Reactant 1

HCID 10829366(2S,3S)-3-(2-aminophenylthio)-2-hydroxy-3-(4-methoxyphenyl)propionamide

Product 1

HCID 27336733-Hydroxy-2-(4-methoxyphenyl)-2,3-dihydro-1,5-benzothiazepin-4(5H)-one, (2S,3S)-Yield 10%

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

A mixture of (2S,3S)-3-(2-aminophenylthio)-2-hydroxy-3-(4-methoxyphenyl)propionamide (159 mg) and xylene (3 ml) is refluxed for 29 hours. After allowed to cool to room temperature, the mixture is stirred to crystallization. The precipitated crystals are collected by filtration, washed with xylene, and dried at 60° C. to give (2S,3S)-2,3-dihydro-3-hydroxy-2-(4-methoxyphenyl)-1,5-benzothiazepin-4(5H)-one (1 15 mg).

Workup

  1. temperatureis refluxed for 29 hours
  2. filtrationThe precipitated crystals are collected by filtration
  3. washwashed with xylene
  4. customdried at 60° C.

Sources & evidence

ORD record
ord-e58d2b47b5a64b259db794e884c41c28
Source dataset
uspto-grants-1998_12
Patent number
US05847122

Reaction notes

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