1-Hydroxybenzotriazole → HCID 10787454, compound

Participants

Reaction Conditions

Reaction Steps

A solution of 2,4-dibenzyloxybenzoic acid (3.34 g) and methyl glycinate hydrochloride (1.25 g) in DMF (40 mL) is treated with triethylamine (2.23 g) and 1-hydroxybenzotriazole (1.53 g) at 0° C. The mixture is stirred for 10 minutes, treated with 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide, hydrochloride (2.05 g) and allowed to warm to 25° C. The solution is evaporated. The residue is partitioned between ethyl acetate and water. The organic layer is washed with 1 M HCl, 1 M NaOH, water, dried and evaporated. The residue is recrystallized from methanol to yield methyl N-(2,4-dibenzyloxybenzoyl)glycinate as a solid (900 mg). H NMR (CDCl3) 3.7(3H,s), 4.2(2H,d), 5.1 (2H,s), 5.2(2H,s), 6.6(1H,s), 6.7(1H,d), 7.3-7.5(10H,m), 8.2(1H,d), 8.4(1H,t).

Provenance & Evidence