Triethylamine → HCID 10389762, compound

Participants

Reaction Steps

To a stirred solution of oxalyl chloride (0.31 mL, 3.56 mmol) in CH2 Cl2 (30 mL) cooled to -60° C. is added DMSO (0.51 mL, 7.12 mmol) dropwise. After 6 min, a solution of 49 (1.11 g, 2.37 mmol) in a mixture of CH2Cl2 (5 mL) and DMSO (3 mL) is slowly added and, 20 min later, Et3N (1.99 mL, 14.25 mmol) is added. The reaction mixture is allowed to warm to room temperature, diluted with CH2 Cl2 (100 mL) and washed with 0.5N aqueous HCl (2×150 mL), and half-saturated aqueous NaHCO3 (2×100 mL) followed by brine (75 mL). Drying (MgSO4) and concentration gives 50 (1.06 g, 96%, mixture of two diastereomers, ratio≈1:1) as a white foam.

Provenance & Evidence