1,2-Dichloroethane → HCID 23589348, compound

Participants

Reaction Conditions

Reaction Steps

2-Hydroxyisocaproic acid (0.143 g, 1.0 mmol) was dissolved in 4 mL of DMF and cooled to 0° C. with an ice-water bath. EDC (0.278 g, 1.4 mmol) and HOBT (0.190 g, 1.4 mmol) were added and stirring, under argon, continued for 25 min. To the cold solution was added 2-amino-3-benzyloxy-propionamide hydrochloride (0.250 g, 1.0 mmol), followed by addition of N-methylmorpholine (0.35 mL, 3.2 mmol) and stirring was continued overnight (16 h). The solution was diluted with 100 mL of EtOAc and washed sequentially with a 1.0 M solution of HCl (3×10 mL), a saturated solution of NaHCO3 (3×10 mL), water (100 mL) and brine (100 mL). The organic layer was dried over MgSO4, filtered and concentrated by rotary evaporation to give (0.17 g, 55%) of the crude product which was chromatographed (SiO2, 3% MeOH in EtOAc) to give the desired product (0.11 g, 35%). (d) Morpholine-4-carboxylic acid 1-(2-benzyloxy-1-carbamoyl-ethylcarbamoyl)-3-methyl-butyl Ester

Provenance & Evidence