Sodium Hydroxide → (1R,3S,4S)-3-[(5-chloro-thiophene-2-carbonyl)-amino]-4-hydroxy-cyclopentanecarboxylic acid

Participants

Reaction Steps

To a stirred suspension of (1R,3S,4S)-3-[(5-chloro-thiophene-2-carbonyl)-amino]-4-hydroxy-cyclopentanecarboxylic acid methyl ester (611 mg; example 1B) in MeOH (4 ml) was added 1N NaOH (4 ml). The reaction mixture which slowly turned into a clear solution was stirred at r.t. for 2 hrs, then concentrated. The residue was dissolved in H2O and washed with Et2O. The aqueous phase was acidified with 3N HCl, then extracted with CH2Cl2/MeOH 9:1. The combined organic layers were washed with H2O and brine, dried over MgSO4 and concentrated to give (1R,3S,4S)-3-[(5-chloro-thiophene-2-carbonyl)-amino]-4-hydroxy-cyclopentanecarboxylic acid (442 mg) as off-white solid. MS: 288.0 ([M−H]−).

Provenance & Evidence