Dicyclohexylcarbodiimide → HCID 56623680, compound

Participants

Reaction Steps

A solution of compound (XX) (19.33 g, 30.0 mmol), glycine methyl ester hydrochloride (see Curtis and Goebel, J. Prakt. Chem., 37:150, (1888)) (3.47 g, 30.0 mmol) and N-hydroxysuccinimide (3.46 g, 30.1 mmol) was cooled to 0° C., then treated with a solution of DCC (6.87 g, 33.4 mmol) in CH2Cl2 (20 ml). The mixture was stirred, cold, for 30 minutes, then at room temperature for 3 hours. The precipitate was filtered off, washed with CH2Cl2, and the combined filtrate and washings were washed with 1M aqueous KHS04, 5% aqueous NaHCO3 and saturated brine, dried (MgSO4) and evaporated. Recrystallization of the resulting solid gave compound (XXI) (12.3 g, 77%), mp 167°-9°.

Provenance & Evidence