Ethyl chloroformate → 2-(3-(4-benzyloxybenzyl)-2-oxoimidazolidin-1-yl)-N-hydroxy-3-methylbutyramide

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Reaction Steps

2-(3-(4-Benzyloxybenzyl)-2-oxoimidazolidin-1-yl)-3-methylbutyric acid (50 mg; 0.13 mmol) was dissolved in tetrahydrofuran (THF; 2 ml). At 0° C., diisopropylethylamine (DIEA; 69 μl; 0.39 mmol) and ethyl chloroformate (25 μl; 0.26 mmol) were successively added. The mixture was allowed to reach RT from 0° C. over the course of 2 h, and then O-trimethylsilylhydroxylamine (50 μl; 0.65 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-benzyloxybenzyl)-2-oxoimidazolidin-1-yl)-N-hydroxy-3-methylbutyramide (25 mg; 0.06 mmol). MS: 398.15 (M+H); Rt: 1.30 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.)

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