Glycine → HCID 2060367, compound

Participants

Reaction Steps

A solution of Z-D-Ala (2.23 g, 10 mmol) and Gly.OMe.HCl (1.26 g, 10 mmol) in THF (50 ml) was chilled to 0° C. and triethylamine (1.01 g, 10 mmol), HOBt (1.35 g, 10 mmol) and DCC (2.06 f, 10 mmol) was added successively at 0° C. with stirring. After stirring for 4 hrs at 0° C., the reaction mixture was stirred at room temperature overnight and the precipitated crystals were filtered and the filtrate was evaporated in vacuo. The residue was extracted with ethyl acetate and the extract was washed with 5% citric acid, 5% NaHCO3 and water successively, and dried over anhyd. Na2SO4. The solvent was removed in vacuo and the resulting solid was recrystallized from ethyl acetate-hexane to give Z-D-Ala-Gly-OMe (26) (2.48 g, 84.4%) as colorless needles, mp 96°-97° C.; [α]D22 23.3° (c=1.0, MeOH): NMR (CDCl3)δ:1.39 (3H, d, J=8 Hz, CH3), 3.76 (3H, s CH3O), 4.03 (2H, d, J=6 Hz, CH2NH), 4.15-4.50 (1H, m, --CH--NH), 5.15, (2H, s, CH2O), 5.58 (1H, d, J=7 Hz, NH), 6.70-6.95 (1H, br, NH), 7.42 (5H, s, Ar--H). Rf (I)=0.62, Rf (VI)=0.38.

Provenance & Evidence