Acetic-formic anhydride → HCID 86756429, compound

Participants

Reaction Conditions

Reaction Steps

A solution of (2R,3S)-3-(2-tetrahydropyranyloxyamino)-2-(2-methyl-1-propyl)hexanoic acid (7.90 g, 27.5 mmol) in 100 mL of anhydrous pyridine is cooled to 0° C. and treated with formic acetic anhydride (4.0 mL, 46 mmol). The reaction mixture is allowed to warm to 25° C., stirred for 6 h, and then concentrated to dryness under reduced pressure. The resulting gum is dissolved in 150 mL of EtOAc and washed successively with two 50-mL portions of 1 M aqueous sodium bisulfate and two 50-mL portions of saturated aqueous sodium chloride. The combined organic extracts are dried over sodium sulfate and filtered, and the solvents are removed under reduced pressure affording 8.67 g (99%) of (2R,3S)-3-(formyl-2-tetrahydropyranyloxyamino)-2-(2-methyl-1-propyl)hexanoic acid obtained as a viscous oil.

Provenance & Evidence