Methanesulfonic Acid → 3-Hydroxy-2-(4-methoxyphenyl)-2,3-dihydro-1,5-benzothiazepin-4(5H)-one, (2S,3S)-

HRID 1457246Notes

Reaction equation

HRID 1457246 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].CS(O)(=O)=O>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

4

Reactant 2

HCID 6395Methanesulfonic AcidHCID 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 93.7%

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

A mixture of (2S,3S)-3-(2-aminophenylthio)-2-hydroxy-3-(4-methoxy-phenyl)propionamide (1.59 g), xylene (8 ml) and methanesulfonic acid (24 mg) is refluxed for 11 hours. After allowed to cool to room temperature, the mixture is stirred to crystallization. The precipitated crystals are collected by filtration, washed with chilled methanol, and dried at 50° C. to give (2S,3S)-2,3-dihydro-3-hydroxy-2-(4-methoxyphenyl)-1,5-benzothiazepin-4(5H)-one (1.41 g).

Workup

  1. temperatureis refluxed for 11 hours
  2. filtrationThe precipitated crystals are collected by filtration
  3. washwashed with chilled methanol
  4. customdried at 50° C.

Sources & evidence

ORD record
ord-c08641b9e6e24408b5b97d22e7fe1b01
Source dataset
uspto-grants-1998_12
Patent number
US05847122

Reaction notes

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