Sodium Hydroxide → 3-hydroxy-2-{[(2-oxo-2,3-dihydro-1H-1,3-benzimidazol-5-yl)carbonyl]amino}propanoic acid

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Reaction Steps

The methyl ester adduct benzimidazol-2-one-5-carboxy-(L-serine)-amide (9) (100 mg, 0.3584 mmol) was suspended in methanol (10 mL) and on addition of 1M aq NaOH (0.68 mL, 0.680 mmol) readily dissolved. The disappearance of starting material was monitored with TLC and complete after stirring overnight at room temperature. The volume was increased by addition of further methanol (30 mL) and the pH carefully adjusted from 10 to 5 by the addition of Dowex 50 W-X8(H+) resin. The resin was rapidly filtered off and washed with further methanol (4×20 mL) and the combined filtrates rotary evaporated to dryness to give benzimidazol-2-one-5-carboxy-(L-serine)-amide (10) (91 mg, 96% yield) as a white powder;

Provenance & Evidence