Acetyl chloride → (+/-)-cis-2-(4-methoxyphenyl)-3-acetoxy-7,8-dimethyl-2,3-dihydro-1,5-benzothiazepin-4(5H)-one

HRID 280528Notes

Reaction equation

HRID 280528 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]=[C:19]([CH3:23])[C:20]([CH3:22])=[CH:21][C:11]=3[S:10]2)=[CH:5][CH:4]=1.[C:24](Cl)(=[O:26])[CH3:25].C(OCC)(=O)C.C(Cl)(Cl)Cl>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:24](=[O:26])[CH3:25])[C:14](=[O:17])[NH:13][C:12]3[CH:18]=[C:19]([CH3:23])[C:20]([CH3:22])=[CH:21][C:11]=3[S:10]2)=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 21584013Chloroform ethylacetateHCID 70409347(+)-cis-2-(4-methoxyphenyl)-3-hydroxy-7,8-dimethyl-2,3-dihydro-1,5-benzothiazepin-4(5H)-one

Product 1

HCID 70484305(+/-)-cis-2-(4-methoxyphenyl)-3-acetoxy-7,8-dimethyl-2,3-dihydro-1,5-benzothiazepin-4(5H)-oneYield 85.9%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

226 mg of (±)-cis-2-(4-methoxyphenyl)-3-hydroxy-7,8-dimethyl-2,3-dihydro-1,5-benzothiazepin-4(5H)-one are suspended in 2 ml of pyridine, and 59 mg of acetyl chloride are added thereto under ice-cooling. The mixture is stirred at room temperature for 2 hours. After the reaction is completed, ethyl acetate-chloroform (1:1) is added to the reaction mixture. The mixture is washed with 10% hydrochlric acid and water, successively. Then, the mixture is dried and evaporated under reduced pressure to remove solvent. 219 mg of (±)-cis-2-(4-methoxyphenyl)-3-acetoxy-7,8-dimethyl-2,3-dihydro-1,5-benzothiazepin-4(5H)-one are obtained.

Workup

  1. temperatureunder ice-cooling
  2. washThe mixture is washed with 10% hydrochlric acid and water
  3. customThen, the mixture is dried
  4. customevaporated under reduced pressure
  5. customto remove solvent

Sources & evidence

ORD record
ord-96de7de26b324c86b366e15cfa438937
Source dataset
uspto-grants-1986_05
Patent number
US04590188

Reaction notes

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