Monomethyl terephthalate → HCID 69817809, compound

Participants

Reaction Steps

To a solution of (2S)-3-(4-aminophenyl)-2-[N-benzyl-N-[(2S)-2-hydroxy-3-phenoxypropyl)amino)-1-propanol (300 mg) in 1,2-dichloroethane (3.0 ml) was added N,O-bis(trimethylsilyl)acetamide (182 μl) and the solution was stirred at room temperature for 1 hour. To the solution were added successively 4-(methoxycarbonyl)benzoic acid (160 mg), 1-hydroxybenzotriazole hydrate (120 mg), and 1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide hydrochloride (170 mg) at room temperature. After stirring at the same temperature for 3 hours, N,O-bis(trimethylsilyl)acetamide (182 μl) was added and the mixture was stirred overnight. The mixture was diluted with ethyl acetate (30 ml) and washed with a saturated aqueous sodium bicarbonate solution (30 ml×1), water (30 ml×2) and brine (30 ml×1) successively, dried over magnesium sulfate, and evaporated to give a yellow solid. The solid was dissolved in tetrahydrofuran (3.0 ml). To the solution was added a 1.0 M solution of tetrabutylammonium fluoride in tetrahydrofuran (1.48 ml) at room temperature and the solution was stirred for 10 minutes. The solution was diluted with ethyl acetate (20 ml) and washed with water (20 ml×2) and brine (20 ml×1) successively, dried over magnesium sulfate, and evaporated to give a yellow solid. The crude product was purified by a recycling preparative high pressure liquid chromatography equipped with a gel permeation chromatography column (eluent: chloroform) and silica gel chromatography (eluent: hexane/ethyl acetate=1/1) to give methyl 4-[[[4-[(2S)-2-[N-benzyl-N-[(2S)-2-hydroxy-3-phenoxypropyl]amino]-3-hydroxypropyl]phenyl]amino]carbonyl]benzoate (132 mg) as a pale yellow solid.

Provenance & Evidence