tert-Butanol → HCID 131734380, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of chlorosulfonyl isocyanate (70.9 μL, 0.82 mmol) at −5° C. in anhydrous DCM (4 mL) was added tert-butanol (solution in 0.5 mL anhydrous DCM) (81 μL, 0.85 mmol) dropwise over 5 min and the reaction stirred at −5° C. for 15 min. After this time, DIPEA (296 μL, 1.70 mmol) was added dropwise. After 15 min a solution of 3,4-bis(benzyloxy)-1-(4-methoxyphenyl)-N,N-dimethyl-1H-pyrrole-2-carboxamide (9) (310 mg, 0.68 mmol) in DCM (1 mL) was added and the reaction was allowed to warm to RT and stirred for 16 h. The reaction was partitioned between water (10 mL) and DCM (20 mL) and the organic washed with 1 M HCl (aq.) (2×20 mL), and brine (10 mL), dried (MgSO4), filtered and solvent removed in vacuo to afford crude product. The residue was purified by silica gel chromatography (40 g, 0-4% MeOH in DCM) to afford tert-butyl (3,4-bis(benzyloxy)-5-(dimethylcarbamoyl)-1-(4-methoxyphenyl)-1H-pyrrol-2-yl)sulfonylcarbamate (10) (166 mg, 35%) as a colourless oil: m/z 636 (M+H)+ (ES+); 634 (M−H)− (ES−).

Provenance & Evidence