Sodium Hydroxide → HCID 13373614, compound

Participants

Reaction Steps

Dissolve 1.05 g of 7-[N-benzyloxycarbonyl-(S)-alanyl]-1,4-dithia-7-azaspiro[4.4]nonane-8(S)-carboxylic acid, methyl ester in 100 ml of methanol. Add 10 ml of 2.5N sodium hydroxide and stir the mixture at room temperature for sixteen hours. Concentrate the mixture under nitrogen, dissolve the oil in 0.1N sodium hydroxide and dilute with ice water. Extract the aqueous solution with ethyl acetate. Acidify the aqueous solution with concentrated hydrochloric acid and then extract with ethyl acetate. Dry the organic phase over magnesium sulfate and concentrate it. Place the residue on a column of silica gel (100 g, 60-200 mesh) and elute with chloroform:glacial acetic acid 19:1 to obtain 7-[N-benzyloxycarbonyl-(S) -alanyl]-1,4-dithia-7-azaspiro-[4.4]nonane-8(S)-carboxylic acid, [α]D26 -15.8° (ethanol).

Provenance & Evidence