4-Methylmorpholine → HCID 69285460, compound

Participants

Reaction Steps

A solution of 3-Trifluoromethyl-benzoic acid (0.55 g, 0.0029 mol) in THF was cooled in an ice bath and treated with N-methylmorpholine (0.3 g, 0.003 mol) and then drop-wise with isobutyl chloroformate (0.39 g, 0.0029 mol). The resulting mixture was stirred for 5 min and then treated with a solution of tert-butyl(1R,3R,4S)-4-(2-aminoacetamido)-3-(hydroxymethyl)cyclohexyl-(isopropyl)carbamate (2.8 g, 0.01 mol) in THF. The resulting mixture was stirred for 30 minutes and then diluted with water and extracted into CH2Cl2. The extract was washed with dilute NaOH, water, and brine and then concentrated under vacuum. The residue was chromatographed on silica gel (elution 55% ethyl acetate/hexane, then 100% ethyl acetate) to give 1.4 g of tert-butyl(1R,3R,4S)-3-(hydroxymethyl)-4-(2-(3-(trifluoromethyl)-benzamido)acetamido)cyclohexyl(isopropyl)carbamate as a white solid. MS found: (M+H)+=516.3.

Provenance & Evidence