Water → benzyl (S)-1-((1S,2R,4R)-2-formamido-4-(isopropyl(methyl)amino)cyclohexyl)-2-oxopyrrolidin-3-ylcarbamate

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Reaction Steps

To 460 mg (10 mmol) of formic acid, acetic anhydride (204 mg, 2 mmol) was added. The mixture was stirred at room temperature for 2 h. Then one fifth of the above solution was added to a mixture of benzyl (S)-1-((1S,2R,4R)-2-amino-4-(isopropyl(methyl)amino)cyclohexyl)-2-oxopyrrolidin-3-ylcarbamate (60 mg, 0.149 mmol) in dichloromethane (3 ml) and triethylamine (62.3 μl, 3 eq) at 0° C. with stirring. The reaction was stirred for 1 h at room temperature and 1 ml of water was added to quench the reaction. The mixture was diluted with dichloromethane (60 ml) and washed with saturated NaHCO3 (20 ml). The solution was dried over anhydrous Na2SO4, filtered, and concentrated in vacuo to give benzyl (S)-1-((1S,2R,4R)-2-formamido-4-(isopropyl(methyl)amino)cyclohexyl)-2-oxopyrrolidin-3-ylcarbamate (50 mg, 78%). LC/MS found [M+H]+=431.

Provenance & Evidence