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

HRID 1381155Notes

Reaction equation

HRID 1381155 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].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: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

5

Reactant 3

HCID 6212ChloroformHCID 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 89.1%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

3.36 g of (-)-cis-2-(4-methoxyphenyl)-3-hydroxy-8-chloro-2,3-dihydro-1,5-benzothiazepin-4(5H)-one are dissolved in 10 ml of pyridine, and 0.87 g of acetyl chloride is added dropwise thereto under ice-cooling. The mixture is stirred at room temperature for one hour. Then, the mixture is diluted by addition of chloroform. The diluted mixture is washed with 10% hydrochloric acid and water, and then evaporated under reduced pressure to remove solvent. The residue is recrystallized from a mixture of ether and n-hexane, whereby 3.37 g of (-)-cis-2-(4-methoxyphenyl)-3-acetoxy-8-chloro-2,3-dihydro-1,5-benzothiazepin-4(5H)-one is obtained as needles.

Workup

  1. temperatureunder ice-cooling
  2. washThe diluted mixture is washed with 10% hydrochloric acid and water
  3. customevaporated under reduced pressure
  4. customto remove solvent
  5. customThe residue is recrystallized from a mixture of ether and n-hexane

Sources & evidence

ORD record
ord-4ca5b05d9c6d47f4b34e6f7c1a770da3
Source dataset
uspto-grants-1986_04
Patent number
US04585768

Reaction notes

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