1,2-Dichloroethane → HCID 54771495, compound

Participants

Reaction Steps

To a mixture of (R)-2-amino-1-((3S,4S)-4-(4-chlorophenyl)-3,4-dihydroxy-3-methylpiperidin-1-yl)-3-methylbutan-1-one (22.49 g, 66.0 mmol), (R)-3,3-difluorocyclopentanecarboxylic acid (10.21 g, 68.0 mmol) in CH2Cl2 (300 mL) and DMF (75 mL) were added HOBT (12.50 g, 82 mmol), EDC (15.65 g, 82 mmol) and Hunig's base (23.76 mL, 136 mmol). The reaction was stirred for 20 h at rt then concentrated to remove the CH2Cl2. Ethyl acetate was added and the organic layer was washed twice with 1N HCl, twice with saturated sodium carbonate and three times with water. The organic layer was dried over sodium sulfate and concentrated to give a glass solid which was crystallized from CH3CN to give (R)—N—((R)-1-((3S,4S)-4-(4-chlorophenyl)-3,4-dihydroxy-3-methylpiperidin-1-yl)-3-methyl-1-oxobutan-2-yl)-3,3-difluorocyclopentanecarboxamide (31.03 g, 65.6 mmol, 99% yield).

Provenance & Evidence