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

HRID 1457248Notes

Reaction equation

HRID 1457248 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C@@H:9]2[O:14][C@H:10]2[C:11]([NH2:13])=[O:12])=[CH:5][CH:4]=1.C1(C)C(C)=CC=CC=1.N[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=1[SH:30].CS(O)(=O)=O>CO>[OH:14][C@H:10]1[C:11](=[O:12])[NH:13][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=2[S:30][C@H:9]1[C:6]1[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=1

Participants

6

Reactant 4

HCID 6395Methanesulfonic AcidHCID 7237O-XyleneHCID 87132-AminothiophenolHCID 10821599(2R,3S)-3-(4-methoxyphenyl)-2,3-epoxypropionamide

Product 1

HCID 27336733-Hydroxy-2-(4-methoxyphenyl)-2,3-dihydro-1,5-benzothiazepin-4(5H)-one, (2S,3S)-Yield 71%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of (2R,3S)-3-(4-methoxyphenyl)-2,3-epoxypropionamide (966 mg) and xylene (10 ml) is refluxed with heating under nitrogen atmosphere. When the reflux is started, a mixture of 2-aminothiophenol (689 mg) and ferrous sulfate heptahydrate (0.11 mg) in methanol (0.1 ml) is added immediately into the reaction system, and the mixture is reacted at the same temperature for 5 minutes. To the reaction mixture is added methanesulfonic acid (48 mg), and the mixture is refluxed for 13 hours. The mixture is cooled with ice for two hours, and the precipitated crystals are collected by filtration, washed with methanol, and dried at 50° C. to give (2S,3S)-2,3-dihydro-3-hydroxy-2-(4-methoxyphenyl)-1,5-benzothiazepin-4(5H)-one (1.07 g).

Workup

  1. temperatureis refluxed
  2. temperaturewith heating under nitrogen atmosphere
  3. additionis added immediately into the reaction system
  4. customthe mixture is reacted at the same temperature for 5 minutes
  5. temperaturethe mixture is refluxed for 13 hours
  6. temperatureThe mixture is cooled with ice for two hours
  7. filtrationthe precipitated crystals are collected by filtration
  8. washwashed with methanol
  9. customdried at 50° C.

Sources & evidence

ORD record
ord-b364b91431ea4407918b5893d17e958b
Source dataset
uspto-grants-1998_12
Patent number
US05847122

Reaction notes

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