Acetyl chloride → (+)-cis-2-(4-methoxyphenyl)-3-acetoxy-8-chloro-2,3-dihydro-1,5-benzothiazepin-4(5H)-one

HRID 1285359Notes

Reaction equation

HRID 1285359 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C@H:9]2[C@@H:15]([OH:16])[C:14](=[O:17])[NH:13][C:12]3[CH:18]=[CH:19][C:20]([Cl:22])=[CH:21][C:11]=3[S:10]2)=[CH:5][CH:4]=1.[C:23](Cl)(=[O:25])[CH3:24]>N1C=CC=CC=1>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C@H:9]2[C@@H:15]([O:16][C:23](=[O:25])[CH3:24])[C:14](=[O:17])[NH:13][C:12]3[CH:18]=[CH:19][C:20]([Cl:22])=[CH:21][C:11]=3[S:10]2)=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 6367Acetyl chlorideHCID 15593400HCID 15593400, compound

Product 1

HCID 70453288(+)-cis-2-(4-methoxyphenyl)-3-acetoxy-8-chloro-2,3-dihydro-1,5-benzothiazepin-4(5H)-oneYield 47.4%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

3 g of (+)-cis-2-(4-methoxyphenyl)-3-hydroxy-8-chloro-2,3-dihydro-1,5-benzothiazepin-4(5H)-one, 0.77 g of acetyl chloride and 20 ml of pyridine are treated in the same manner as described in Preparation 7. The crude product is recrystallized from a mixture of ether and n-hexane. 1.6 g of (+)-cis-2-(4-methoxyphenyl)-3-acetoxy-8-chloro-2,3-dihydro-1,5-benzothiazepin-4(5H)-one are thereby obtained as colorless needles.

Workup

  1. customas described in Preparation 7
  2. customThe crude product is recrystallized from a mixture of ether and n-hexane

Sources & evidence

ORD record
ord-b228097428d64bdbbbd85a0e9dc70652
Source dataset
uspto-grants-1986_01
Patent number
US04567175

Reaction notes

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