Oxalyl chloride → HCID 86584828, compound

Participants

Reaction Conditions

Reaction Steps

A solution of 25 g (93 mmol) (2S,4R)-1-methanesulfonyl-4-tritylsulfanyl-pyrrolidine-2-carboxylic acid in 265 ml CH2Cl2 at 0° C. was treated with 2 drops of DMF followed by 8 ml (99 mmol) oxalylchloride. After 15 min at 0° C. the reaction was stirred 2 h at room temperature, evaporated and dissolved in 260 ml THF/CH3CN 1:1. 58.5 ml (117 mmol) 2M trimethylsilyldiazomethane solution in hexane was then added at 0° C. The reaction was stirred 16 h at room temperature, evaporated and poured in H2O/EtOAc. The organic phase was dried over Na2SO4, evaporated and purified by flash column chromatography on silica gel with hexane/EtOAc (7:3 to 1:1) to give 12.4 g (48%) of (2S,4R)-2-diazo-1-(1-methanesulfonyl-4-tritylsulfanyl-pyrrolidin-2-yl)-ethanone, MS: 509 (M+NH4+).

Provenance & Evidence