Diisopropylethylamine → HCID 131725921, compound

Participants

Reaction Steps

To 1-cyclopentyl-3-methylsulfonylthiourea (200 mg, 0.89 mmol, 2.4 equiv.), 2-amino-N-[1-(benzoxazol-2-ylhydroxymethyl)-propyl]-3-cyclopropylmethanesulfonyl-propionamide (163 mg, 1.0 equiv.), N-methyl-2-chloropyridinium iodide (175 mg, 1.8 equiv.) in 4 mL dichloromethane was added DIPEA (142 mg, 2.8 equiv). The reaction mixture was stirred overnight at ambient temp. The reaction was diluted with ethyl acetate and extracted with saturated sodium bicarbonate, brine and dried over MgSO4. Purification by column chromatography (EtOAC/hexanes) afforded N-[1-(benzoxazol-2-ylhydroxymethyl)propyl]-2-(1-cyclopentylamino-2-methanesulfonylvinylamino)-3-cyclopropylmetanesulfonylpropionamide as a mixture of diastereomers (41 mg, M=584.3 M+1) which was oxidized to the title compound using Dess-Martin Periodane as previously described.

Provenance & Evidence