4-Methylmorpholine → HCID 86596968, compound

Participants

Reaction Steps

A solution of 3-Trifluoromethyl-benzoic acid (0.23 g, 0.0012 mol) in THF was cooled in an ice bath and treated with N-methylmorpholine(0.13 g, 0.0013 mol) and then drop-wise with isobutyl chloroformate (0.16 g, 0.0012 mol). The resulting mixture was stirred for 5 min and then treated with a solution of isopropyl (1R,2S,5R)-2-(2-aminoacetamido)-5-(tert-butoxycarbonyl-isopropyl-amino)cyclohexanecarboxylate (0.45 g, 0.0011 mol; See Example 8b, Step 4) 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) to give 0.4 g of isopropyl(1R,2S,5R)-5-(tert-butoxycarbonyl-isopropyl-amino)-2-(2-(3-trifluoromethyl-benzamido)acetamido)cyclohexanecarboxylate as a white solid, MS found: (M+H)+=572.4.

Provenance & Evidence