Water → HCID 21545310, compound

Participants

Reaction Steps

To a solution of N-tritylglycine (25.6 g) and triethylamine (14.0 ml) in dimethylformamide (DMF) (60 ml), a solution of chloroiodomethane (24.0 ml) in DMF (40 ml) was added dropwise while stirring, and the mixture was stirred for 3.5 hours at room temperature. Then the mixture was poured into water (400 ml), the organic phase was separated, and the aqueous phase was extracted with ethyl acetate. The combined organic phases were washed with water and thereafter twice with aqueous sodium bicarbonate and again with water. The organic phase was dried and evaporated in vacuo to yield the crude ester. TLC: Rf = 0.7 (cyclohexane-ethyl acetate, 1:1), ir )CHCl3): 1765 cm-1 (ester carbonyl), nmr (CDCl3 -TMS standard): δ = 3.20 (s), 5.53 (s), 7.00-7.30 (m) ppm.

Provenance & Evidence