Dimethyl Sulfoxide → HCID 57066216, compound

Participants

Reaction Steps

To a solution of 0.1 mL (1.15 mmol) of oxalyl chloride in 2 mL of CH2Cl2 cooled in a −78° C. bath, 0.1 mL (1.41 mmol) of dry DMSO was added. After 0.5 hr, a solution of 0.26 g (0.59 mmol) of 2(S)-(3-(R)-hydroxymethyl-4-(S)-(3-fluorophenyl)pyrrolidin-1-yl)-3-ethylvaleric acid, 4-methoxybenzyl ester (step D) in 2.5 mL of CH2Cl2 was added. After 0.5 hr, 0.5 mL (3.57 mmol) of triethylamine was added to the reaction and the cold bath was removed. After stirring for 2 hr, the reaction was partitioned between water and CH2Cl2. The organic layer was washed with brine, dried and concentrated. The residue was purified on a flash column using a gradient of 20-30% EtOAc in hexane to isolate 0.23 g of the title compound. 1H NMR (CDCl3) 0.86 (m, 6H), 1.2-1.8 (m, 5H), 2.82 (m, 2H), 3.05 (t, 1H), 3.18 (m, 2H), 3.32 (d, 1H), 3.52 (m, 1H), 3.83 (s, 3H), 5.13 (s, 2H), 6.9-7.4 (m, 8H), 9.64 (d, 1H).

Provenance & Evidence