Dimethyl Sulfoxide → HCID 131722701, compound

Participants

Reaction Conditions

Reaction Steps

Oxalyl chloride (0.022 mL, 0.25 mmol) was added to 5 mL of CH2Cl2 in a dry flask under nitrogen. The solution was cooled to −78° C., DMSO (0.040 mL, 0.57 mmol) was added, and the reaction mixture was stirred for 15 minutes. A solution of 2-(R)-(2-Methyl-3-(R)-hydroxymethyl-4-(S)-(3-fluorophenyl)pyrrolidin-1-yl)-3-(cyclopropyl)propionic acid, benzyl ester (88 mg, 0.21 mmol, from Step C) in 0.75 mL of CH2Cl2 was added, and the reaction mixture was stirred at −78° C. for 30 min. Triethylamine (0.153 mL, 1.1 mmol) was added and the reaction mixture was warmed to room temperature, diluted with CH2Cl2 and washed twice with 1N NaOH and brine. The solution was dried over Na2SO4, filtered and concentrated to provide 54 mg (63% yield) of the title compound. 1H NMR (400 MHz, CDCl3) δ0.02-0.19 (m, 2H), 0.39-0.55 (m, 2H), 0.78-0.86 (m, 1H), 1.28 (d, 3H), 1.50-1.57 (m, 1H), 1.78-1.85 (m, 1H), 2.60-2.66 (m, 1H), 3.05-3.15 (m, 2H), 3.36-3.47 (m, 2H), 3.69-3.75 (m, 1H), 5.15-5.26 (m, 2H), 6.89-6.96 (m, 1H), 7.00-7.04 (m, 2H), 7.21-7.30 (m, 1H), 7.32-7.43 (m, 5H), 9.57 (d, 1H); ESI-MS (M+H): 410.3; HPLC A: 2.54 min.

Provenance & Evidence