Dimethyl Sulfoxide → HCID 86706199, compound

Participants

Reaction Conditions

Reaction Steps

To a round bottom dry flask was added DCM (2 mL), and a 2 M solution of oxalyl chloride in DCM (0.100 mL, 0.200 mmol). The reaction was cooled to −78° C. Then slowly was DMSO (0.028 mL, 0.401 mmol) added over 5 min. The reaction was stirred at −78° C. for 30 min. Then (R)-(9H-fluoren-9-yl)methyl 1-(5-hydroxypentylamino)-3-methyl-1-oxo-3-(tritylthio)butan-2-ylcarbamate (100 mg, 0.143 mmol) in DCM (3 mL) was added to the reaction over 5 min and the reaction was stirred at −78° C. for 45 min. Then TEA (0.088 mL, 0.630 mmol) was added to the reaction and the reaction was stirred for additional 30 min at −35° C. The reaction was quenched with EtOAc (2 mL). The reaction was diluted with EtOAc (20 mL) and washed with saturated aqueous NaHCO3 (10 mL), water (10 mL) and saturated aqueous NaCl (10 mL). The organic layer was separated, dried over MgSO4, filtered and concentrated to give (R)-(9H-fluoren-9-yl)methyl 3-methyl-1-oxo-1-(5-oxopentylamino)-3-(tritylthio)butan-2-ylcarbamate (95 mg, 0.14 mmol, 95% yield).

Provenance & Evidence