tert-Butanol → HCID 68839874, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of chlorosulfonylisocyanate (346 mg, 2.45 mmol) in CH2Cl2 (15 mL) at 0° C. is added dropwise a solution of t-butanol (181 mg, 2.45 mmol) in CH2Cl2 (5 mL) and the mixture is stirred at 0-5° C. for 30 min. To this is added dropwise a solution of methyl (4-benzenesulfonyl-2-benzyloxyphenylamino)acetate (620 mg, 1.63 mmol) and triethylamine (281 mg, 278 mmol) in CH2Cl2 (5 mL) and the mixture is stirred at RT for 4 h. The mixture is washed with water and the organic layer is dried over magnesium sulfate. The solvent is removed under reduced pressure to afford an oil that is chromatographed on a Biotage 40M column using CH2Cl2/EtOAc (95:5) as eluent to afford the title compound as an oil: 1H NMR (CDCl3) δ 7.82 (m, 3H), 7.47 (m, 11H), 5.24 (s, 2H), 4.54 (br s, 2H), 3.67 (s, 3H), 1.41 (s, 9H); (M−1)−=589.

Provenance & Evidence