(S,S,S)-7-[2-[(1-ethoxycarbonyl-3-phenylpropyl)amino]-1-oxopropyl]-1,4-dithia-7-azaspiro[4.4]nonane-8-carboxylic acid, diphenylmethyl ester → Spirapril

Participants

Reaction Steps

A solution of (S,S,S)-7-[2-[(1-ethoxycarbonyl-3-phenylpropyl)amino]-1-oxopropyl]-1,4-dithia-7-azaspiro[4.4]nonane-8-carboxylic acid, diphenylmethyl ester (800 mg.) in a mixture of trifluoroacetic acid (15 ml.) and anisole (3 ml.) is stirred at 0° for 30 minutes. The solvent is removed at reduced pressure and the residue applied to an AG 50W-X2(H+) column. After washing with water, the column is eluted with aqueous pyridine. The fractions containing the product are combined and lyophilized to yield (S,S,S)-7-[2-[(1-ethoxycarbonyl-3-phenylpropyl)amino]-1-oxopropyl]-1,4-dithia-7-azaspiro[4.4]nonane-8-carboxylic acid.

Provenance & Evidence