Cyclohexanone → HCID 13454619, compound

Participants

Reaction Steps

A mixture of 3(R)-[5-amino-1(S)-ethoxycarbonylpentyl]amino-4-oxo-2,3,4,5-tetrahydro-1,5-benzothiazepine-5-acetic acid dihydrochloride (0.2 g) obtained in Example 59, ethanol (10 ml), cyclohexanone (2 g) and sodium cyanoborohydride (0.3 g) is allowed to stand overnight at room temperature. To the residue, after evaporation of ethanol, is added 1N aqueous sodium hydroxide (4 ml). The resulting mixture is stirred at room temperature for 1 hour, diluted with water (20 ml) and extracted 3 times with ethyl acetate (20 ml each). The aqueous layer is slightly acidified with acetic acid (1 ml) and subjected to Amberlite XAD-2 column chromatography eluting with methanol-water (1:1). The eluate is concentrated under reduced pressure and lyophilized to give 3(R)-[1(S)-carboxy-5-cyclohexylaminopentyl]amino-4-oxo-2,3,4,5-tetrahydro-1,5-benzothiazepine-5-acetic acid (0.12 g) as colorless powder.

Provenance & Evidence