Diisopropylethylamine → Ethyl 2-benzyl-3-hydrazinyl-2-hydroxy-3-oxopropanoate

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Reaction Steps

A mixture of 2-benzyl-3-ethoxy-2-hydroxy-3-oxopropanoic acid (250 mg), HATU (479 mg), diisopropylethyl amine (149 mg) and N-hydroxysuccinamide (145 mg) in 4 mL of DMF was stirred at ambient temperature for 1.5 h. The mixture was diluted with ethyl acetate, washed with water. The organic layer was dried with magnesium sulfate and concentrated to give the desired product ethyl 2-benzyl-3-hydrazinyl-2-hydroxy-3-oxopropanoate (352 mg), which was directly used for the next step. To ethyl 2-benzyl-3-hydrazinyl-2-hydroxy-3-oxopropanoate (352 mg) in DCM (5 mL) was added hydrazine (anhydrous, 101 mg) at ambient temperature. Instantaneously the solution turned cloudy and after 15 min the solvent was removed in vacuo to afford the crude title compound as an amorphous solid. LC/MS 275.2 (M+23).

Provenance & Evidence