Phosphoric Acid → HCID 14520033, compound

Participants

Reaction Steps

A solution of oxalyl chloride (0.51 mL, 5.8 mmol) in CH2Cl2 (6 mL) was added dropwise to a suspension of 6-methoxy-2-(phenylmethoxy)-5-(trifluoromethyl)-1-naphthalenecarboxylic acid (2.00 g, 5.3 mmol, described in Example 8) in 50 mL of CH2Cl2 under a nitrogen atmosphere. The suspension became homogeneous upon stirring for 1.5 hours. The mixture was then placed under mild vacuum for about 5 minutes to remove the dissolved gases and then was transfered via syringe to a flask containing a suspension of N-methylglycine methyl ester hydrochloride (11.1 g, 8.0 mmol) and triethylamine (3.7 mL, 27 mmol) in 50 mL of CH2Cl2. The suspension was stirred for 20 hours then was poured into additional CH2Cl2 and 1M H3PO4. The organic phase was separated and washed successively with 1M H3PO4, water, saturated NaCl and then dried over Na2SO4. After filtration, concentration and silica gel chromatography with 20:1 CH2Cl2 :ethyl acetate as eluent, the residue was recrystallized from ethanol to give 1.51 g (62% yield) of the title compound as a white powder, m.p. 95°-98° C.

Provenance & Evidence