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

HRID 1418722Notes

Reaction equation

HRID 1418722 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-methoxyphenyl)propioamide (1.59 g), xylene (8 ml) and methanesulfonic acid (24 ml) is refluxed for 11 hours. The reaction solution is allowed to cool to room temperature with stirring. The precipitated crystals are collected by filtration, washed with cold methanol, and dried at 50° C. to give (2S,3S)-2,3-dihydro-3-hydroxy-2-(4-methoxyphenyl)-1,5-benzothiazepine-4(5H)-one (1.41 g).

Workup

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

Sources & evidence

ORD record
ord-7d3ed277c820496092f22819da8ac879
Source dataset
uspto-grants-1999_03
Patent number
US05883264

Reaction notes

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