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

HRID 1457251
Notes
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Reaction equation

HRID 1457251 reaction equation
COC1C=CC([C@@H]2O[C@H]2C(N)=O)=CC=1.NC1C=CC=CC=1S.N[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=1[S:30][C@@H:31]([C:37]1[CH:42]=[CH:41][C:40]([O:43][CH3:44])=[CH:39][CH:38]=1)[C@@H:32]([OH:36])[C:33]([NH2:35])=[O:34].O.C1(C)C=CC(S(O)(=O)=O)=CC=1>CO.ClC1C=CC=CC=1>[OH:36][C@H:32]1[C:33](=[O:34])[NH:35][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=2[S:30][C@H:31]1[C:37]1[CH:42]=[CH:41][C:40]([O:43][CH3:44])=[CH:39][CH:38]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 87132-AminothiophenolHCID 521998p-Toluenesulfonic acid monohydrateHCID 10821599(2R,3S)-3-(4-methoxyphenyl)-2,3-epoxypropionamideHCID 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)-

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 7964ChlorobenzeneSolvent

Procedure

A mixture of (2R,3S)-3-(4-methoxyphenyl)-2,3-epoxypropionamide (9.66 g) and chlorobenzene (193 ml) is refluxed with heating under nitrogen atmosphere. When the reflux is started, a solution of 2-aminothiophenol (6.89 g) and ferric chloride hexahydrate (1.35 mg) in methanol (0.1 ml) is added immediately into the reaction mixture, and the mixture is stirred at the same temperature for 5 minutes. The reaction mixture containing (2S,3S)-3-(2-aminophenylthio)-2-hydroxy-3-(4-methoxyphenyl)propionamide is refluxed for 15 hours during which p-toluenesulfonic acid monohydrate (2.88 g) is added thereto in 6 portions (0.48 g×6) at intervals of 2.5 hours to remove the chlorobenzene. The remaining chlorobenzene is evaporated, and methanol (50 ml) is added to the residue. The mixture is refluxed for one hour, allowed to cool to room temperature, and further cooled at 3° C. overnight. 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 (11.73 g).

Workup

  1. temperatureis refluxed
  2. temperaturewith heating under nitrogen atmosphere
  3. additionis added
  4. customin 6 portions (0.48 g×6) at intervals of 2.5 hours to remove the chlorobenzene
  5. customThe remaining chlorobenzene is evaporated
  6. additionmethanol (50 ml) is added to the residue
  7. temperatureThe mixture is refluxed for one hour
  8. temperaturefurther cooled at 3° C. overnight
  9. filtrationThe precipitated crystals are collected by filtration
  10. washwashed with chilled methanol
  11. customdried at 50° C.

Sources & evidence

ORD record
ord-a8ff6bf25e644325b63b566aec29718d
Source dataset
uspto-grants-1998_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05847122

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes