Ethyl chloroformate → HCID 11717921, compound

Participants

Reaction Steps

2-(3-(4-Benzyloxyphenyl)-2-oxoimidazolidin-1-yl)-3-methylbutyric acid (66 mg; 0.18 mmol) was dissolved in THF (2 ml). At 0° C., diisopropylethylamine (DIEA; 124 μl; 0.71 mmol) and ethyl chloroformate (51 μl; 0.53 mmol) were successively added. The mixture was allowed to reach RT from 0° C. over the course of 2 h and then O-trimethylsilylhydroxylamine (80.43 μl; 1.07 mmol) was added. Stirring at RT for a further 3 h was followed by partitioning between dilute HCl (10 ml) and EtOAc (10 ml). The phases were separated and the aqueous phase was extracted with EtOAc (3×; 5 ml). The combined organic phases were dried over MgSO4. The solvent was removed under reduced pressure. Trituration of the residue with EtOAc (2 ml) resulted in 2-(3-(4-benzyloxyphenyl)-2-oxoimidazolidin-1-yl)-N-hydroxy-3-methylbutyramide (22 mg; 0.06 mmol). MS: 384.25 (M+H); Rt: 1.94 min (method: gradient acetonitrile+0.08% formic acid: H2O+0.1% formic acid from 5:95 (0 min) to 95:5 (2.5 min) to 95:5 (3 min); flow rate 1.3 ml/min; column YMC Jsphere 33*2.1)

Provenance & Evidence