Acetic Acid → HCID 178442068, compound

Participants

Reaction Steps

To a solution of Boc-Asn(Trt)-OH (101 mg, 0.213 mmol) in acetonitrile (2.0 mL) cooled in an ice water bath was added 4-methylmorpholine (0.059 mL, 0.53 mmol) and isobutyl chloroformate (0.027 mL, 0.21 mmol). After stirring for 45 minutes 4-neopentylbenzene-1,2-diamine (Preparation 83, 34 mg, 0.19 mmol) was added and the mixture allowed to warm to room temperature. After stirring for 2.5 hours, the reaction mixture was concentrated in vacuo and acetic acid (1.0 mL, 18 mmol) was added. The reaction was stirred for 18 hours, concentrated in vacuo, redissolved in ethyl acetate, washed with water, aqueous saturated sodium hydrogen carbonate solution, and brine. The organic layer was dried over anhydrous magnesium sulfate, filtered and concentrated in vacuo. The residue was purified by silica gel column chromatography eluting with a 0-100% ethyl acetate/hexanes gradient to afford the title compound (108 mg, 93%) as an off white solid that was taken directly on to the next step.

Provenance & Evidence