Benzaldehyde → HCID 86600964, compound

Participants

Reaction Conditions

Reaction Steps

N-[(R)-2-(Hydrazinocarbonyl)-heptyl]-N-hydroxy-formamide (50 mg, 0.23 mmoles) and benzaldehyde (24 mg, 0.23 mmoles) were dissolved in methanol (2 mL) under argon in the. presence of 4 Å molecular sieves (50 mg), stirred for 1 hour and cooled to 0° C. To the mixture was added one crystal of methyl orange indicator and enough methanolic HCl to keep the solution acidic (red color). Sodium cyanoborohydride (17 mg, 0.28 mmoles) was added, along with enough methanolic HCl to keep the solution acidic (red indicator). The system was warmed to room temperature, stirred for two days, neutralized with sodium bicarbonate solution, and extracted with ethyl acetate (3×). The organic layer was dried over anhydrous sodium sulfate, concentrated to dryness and purified by prep hplc to afford the title compound. MH+308.

Provenance & Evidence