Diisopropylethylamine → HCID 86619841, compound

Participants

Reaction Conditions

Reaction Steps

2-(3-Benzyl-5-(4-methoxyphenyl)-2-oxoimidazolidin-1-yl)-3-methylbutyric acid (150 mg; 0.39 mmol) was introduced into DMF (10 ml) and cooled to 0° C. Then N,N-diisopropylethylamine (202 mg; 1.56 mmol), O-benzylhydroxylamine hydrochloride (125 mg, 0.78 mmol) and O-(7-azabenzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate (HATU; 223 mg; 0.58 mmol) were added, and the mixture was stirred at 0° C. for 2 h. The reaction solution was then concentrated and partitioned between dilute HCl solution/EtOAc and extracted with EtOAc (2×). The combined organic phases were dried over MgSO4, and the solvent was removed in a rotary evaporator. Purification by chromatography resulted in 2-(3-benzyl-5-(4-methoxyphenyl)-2-oxoimidazolidin-1-yl)-N-benzyloxy-3-methylbutyramide (116 mg; 0.24 mmol). MS: 488.25 (M+H); Rt: 3.50 min (method: gradient 95% H2O (0.05% TFA) to 95% acetonitrile over 3.5 min, 95% acetonitrile for 1.0 min, 5% acetonitrile 1.0 min; flow rate 0.5 ml/min; column 1 μL (Merck Purospher 5μ 2×55 mm); 30° C.)

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