Phosgene → HCID 86619837, compound

Participants

Reaction Conditions

Reaction Steps

t-Butyl (R)-2-(2-(3-benzyloxybenzylamino)ethylamino)-3-methylbutyrate (155 mg; 0.37 mmol) was dissolved in toluene (5 ml) and cooled to 0° C. NaOH (1N; 5 ml; 5 mmol) was added, as was phosgene (20% in toluene; 0.37 ml; 0.75 mmol). The mixture was stirred at 0° C. for 6 h, the phases were separated, and the aqueous phase was extracted with CH2Cl2 (2×; 5 ml). The combined organic phases were dried over MgSO4, and the solvents were removed under reduced pressure. Purification of the residue by column chromatography (SiO2) resulted in t-butyl (R)-2-(3-(3-benzyloxybenzyl)-2-oxoimidazolidin-1-yl)-3-methylbutyrate (102 mg; 0.23 mmol). MS: 439.25 (M+H); Rt: 2.12 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