Hydrochloric Acid → HCID 86619839, compound

Participants

Reaction Conditions

Reaction Steps

t-Butyl (R)-2-(3-(3-benzyloxybenzyl)-2-oxoimidazolidin-1-yl)-3-methylbutyrate (102 mg; 0.23 mmol) was dissolved in CH2Cl2 (2 ml) and cooled to 0° C. Trifluoroacetic acid (TFA; 1 ml) was added, and the mixture was stirred for 2 h. The solvents were removed under reduced pressure, and the residue was taken up in tetrahydrofuran (THF; 2 ml). DIEA (0.16 ml; 0.93 mmol) and ethyl chloroformate (67 μl; 0.69 mmol) were added. After stirring at RT for 2 h, O-trimethylsilylhydroxylamine (0.10 ml; 1.39 mmol) was added. The mixture was stirred for 15 h, HCl (6N, 0.30 ml) was added, and then the solvents were removed under reduced pressure. Purification of the residue by preparative HPLC resulted in (R)-2-(3-(3-benzyloxybenzyl)-2-oxoimidazolidin-1-yl)-N-hydroxy-3-methylbutyramide (8 mg, 0.02 mmol). MS: 398.15 (M+H); Rt: 1.46 min (method: gradient 0 min 96% H2O (0.05% TFA) 2.0 min 95% acetonitrile, 95% acetonitrile to 2.4 min, 4% acetonitrile 2.45 min; flow rate 1 ml/min; column 0.4 μL (YMC J'sphere ODS H80 20X2 1.4μ); 30° C.)

Provenance & Evidence