Sodium Hydroxide → HCID 53761674, compound

Participants

Reaction Steps

A mixture of compound XXVI (200 mg, 0.53 mmol), 0.6N aqueous sodium hydroxide (1.34 ml, 0.80 mmol) and 4 ml of methyl alcohol was stirred at room temperature for 16 hours. The reaction mixture was poured onto 15 ml of ice water and was washed with diethyl ether. The aqueous layer was acidified with 1N aqueous hydrochloric acid to pH 4.0, then saturated with sodium chloride. The saturated solution then was extracted four times with 5 ml portions of ethyl acetate. The combined organic extracts were washed with the 5 ml portions of water, dried over anhydrous magnesium sulfate, then filtered. Evaporation of solvent in vacuo gave a crude acid that was then purified on 20 g of silica gel. Elution with ethyl acetate:acetic acid, 95:5, provided 121 mg (63%) of acid (XXVII), having Rf :0.28 (ethyl acetate:acetic acid, 95:5).

Provenance & Evidence