Ethylene Glycol → HCID 69677444, compound

Participants

Reaction Conditions

Reaction Steps

Dry hydrogen chloride (68.3 g) was dissolved in ethylene glycol (994 mL) at <20° C. and then solid 4-nitro-(S)-phenylalanine (198.7 g) added with stirring. The mixture was heated to 80-85° C. and held at this temperature for 2 h. After a LC completion check, the preparation was allowed to drift to 60° C. and seeded with authentic product. Once crystallisation had initiated, the resulting suspension was cooled further to 20° C. and stirred out overnight. The 4-nitro(S)-phenylalanine hydroxyethyl ester hydrochloride was collected by filtration, washed in situ with dimethoxyethane (795 mL), and then dried in vacuo at 40-45° C. to constant weight (white powder m.p. 195-197° C., 187.0 g, 73.9% yield). 1H NMR (D6-DMSO): δ3.27 (2H, ddd); 3.42 (2H, m); 4.01 (2H, m); 4.27 (1H, t); 4.88 (1H, b,s); 7.52 (2H, d); 8.11 (2H, d); 8.76 (3H, b,s) ppm. Mass Spectrum: ESI+ (m/z+1) 255.0

Provenance & Evidence