Potassium Hydroxide → HCID 69072340, compound

Participants

Reaction Steps

KOH (5 mL of a 1M solution in ethanol) was added to a solution of ethyl 3-{5-tert-butoxy-4-({6-[(tert-butoxycarbonyl)amino]pyridin-3-yl}methyl)-3-[(4-methoxybenzyl)thio]-5-oxopentyl}benzoate (0.27 g, 0.406 mmol, synthesised according to the procedure for Example 1) in ethanol (2 mL), and the mixture was stirred at room temperature for 2 h and then at 50° C. for 2 h. The reaction mixture was then diluted with diethyl ether and water. The organic phase was extracted with 0.1M aqueous KOH and the combined aqueous phase was acidified (pH 5) using 3M aqueous HCl. The aqueous phase was then extracted with diethyl ether and the organic phase was washed with brine, dried and concentrated. Purification of the residue by reversed-phase HPLC (C-8 column, linear gradient 40%→100% of MeCN in 5% aqueous MeCN containing 0.1 M ammonium acetate) gave a residue that was dissolved in toluene and water and concentrated to give 3-{5-tert-butoxy-4-({6-[(tert-butoxycarbonyl)amino]pyridin-3-yl}methyl)-3-[(4-methoxybenzyl)thio]-5-oxopentyl}benzoic acid (0.12 g, 54%).

Provenance & Evidence