m-Chloroperbenzoic acid → HCID 131734945, compound

Participants

Reaction Steps

Added m-CPBA 50% (1.92 gm, 5.56 mmol) in portions to an ice-cooled solution of tert-butyl (2-chloro-5-cyano-3-vinylphenyl)carbamate (Example 399A)(517 mg, 1.86 mmol) in DCM (30 mL). The bath was removed and the reaction was left stirring at room temperature overnight. Added additional 50% MCPBA (0.6 gm) and left stirring overnight. Added 20 mL of 0.5 M NaHCO3 solution and left stirring for 4 hr. The aqueous phase was separated and washed with DCM. The combined organic phases were washed three times with 1 N Na2CO3 solution. After drying with sodium sulfate, the solvents were removed to leave crude tert-butyl (2-chloro-5-cyano-3-(oxiran-2-yl)phenyl)carbamate (516 mg, 94% yield). This was dissolved in a mixture of DCE (12 mi) and MeOH (6 mL) in a microwave vial. Ethanolamine (2.12 mL, 35.0 mmol) was added and the vial was sealed and heated at 60° C. overnight. The solvent was removed and the residue was taken up in DCM and washed with water (2×) and brine. After drying with sodium sulfate, the solvent was removed and radial silica gel chromatography eluting with DCM containing 0 to 14% MeOH and then 10% 2N NH3 in MeOH afforded tert-butyl (2-chloro-5-cyano-3-(1-hydroxy-2-((2-hydroxyethyl)amino)ethyl)phenyl)carbamate (337 mg).

Provenance & Evidence