Triethylamine → HCID 131730205, compound

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of 3-(benzyloxy)-2,2-dimethylpropanoic acid from Step B (415 mg, 1.99 mmol) in DCM (20 mL) was added one drop of DMF (cat.) followed by the drop wise addition of oxalyl chloride (329 mg, 2.59 mmol) over 10 minutes, while at ambient temperature. After the evolution of gas has ceased, the reaction was cooled to 0° C., prior to the introduction of ethyl anilinoacetate (429 mg, 2.39 mmol) and triethylamine (302 mg, 2.99 mmol). After 2 hours at 0° C., the reaction was allowed to warm to ambient temperature and then stir for an additional 1 hour. The reaction mixture was applied directly to a silica gel column for purification, eluting with a gradient of CH2Cl2:MeOH—99.5:0.5 to 98:2. Product containing fractions were pooled and concentrated in vacuo to give the title compound. MS: m/z=370 (M+1).

Provenance & Evidence