Acetic Acid → HCID 57808413, compound

Participants

Reaction Conditions

Reaction Steps

A 7 mL glass vial was charged with 500 μL water and cooled to 0° C. Sodium nitrite (1.8 mg, 0.026 mmol, 180 μL of 10 mg/mL aqueous solution), 1M hydrochloric acid (52 μL, 0.052 mmol) and acetic acid (0.039 mmol, 2.3 mg, 230 μL of 10 mg/mL aqueous solution) were added sequentially and stirred for ca. five minutes. A solution of acyl hydrazide 14 (5 mg in 500 μL THF:200 μL H2O, 0.013 mmol) was added slowly and the reaction mixture was stirred at 0° C. for 10 minutes. The acidic solution was neutralized with saturated sodium bicarbonate (2 mL) and extracted with cold diethyl ether (3×2 mL). The organic fractions were collected in a second 20 mL vial at 0° C., and 270 μL of a cold, ethereal solution of L-valinol (10 mg/mL, 0.026 mmol, 2.7 mg) was added slowly. The reaction was allowed to warm to room temperature, and stirred overnight. The solvent was evaporated, and the product was purified by silica gel chromatography (9.4:0.6:0.1% DCM:MeOH:Et3N, Rf=0.35) to give 5 mg (86% yield) of a colorless oil. MS: (ESI-TOF) MH+ expected: 448.3282, found: 448.3283.

Provenance & Evidence