Preparation of benzyl anthranilate_Kain Industrial Additive

Background and overview^[1]

Benzyl anthranilate can be used as a pharmaceutical synthesis intermediate. If benzyl anthranilate is inhaled, move the patient to fresh air; if the skin comes in contact, take off contaminated clothing, rinse the skin thoroughly with soap and water, and seek medical attention if you feel uncomfortable; if in contact with the eyes, remove the contaminated clothing. The eyelids should be separated, rinsed with running water or saline, and seek medical attention immediately; if ingested, rinse mouth immediately, do not induce vomiting, and seek medical attention immediately.

Preparation^[1]

Preparation of benzyl anthranilate is as follows: combine isatoic anhydride (8.54g), benzyl alcohol (6.0g), 4-dimethylaminopyridine (6.7g), dimethylformamide (17ml), A mixture of triethylamine (5.28g) and dichloromethane (160ml) was refluxed overnight and washed with equal volumes of ethyl acetate, water, brine and water. The organic solution was dried over magnesium sulfate, filtered, and concentrated in vacuo. The crude product was purified by flash chromatography, eluting with 30% ethyl acetate in hexane, to give the desired product.

Application

Benzyl anthranilate can be used to prepare 2-[(N-tert-butoxycarbonyl-L-prolyl)amino]benzoate benzyl ester: to N-tert-butoxycarbonyl-L-proline To a solution of acid (0.5g) in dichloromethane (4ml) were added N-methylpiperidine (0.19ml) and a solution of benzyl 2-aminobenzoate (1.0M). in toluene, 1.4 ml). After stirring the solution for approximately 2 minutes at 0°C, D-leucyl-D-aspartic acid amide benzyl ester trifluoroacetate (1.4 mmol) and N-methylpiperidine (0.31 g) were dissolved in dichloro A solution of methane (4 ml) was added and the solution was stirred at 0 °C for approximately 2 h and then at room temperature overnight.

The solution was diluted with ethyl acetate, and the organic layer was washed with water, 1N hydrochloric acid, and 10% sodium carbonate solution, then dried over magnesium sulfate, filtered, and concentrated in vacuo. The crude product was purified by flash chromatography eluting with 15% ethyl acetate in hexane to give the desired product 2-[(N-tert-butoxycarbonyl-L-prolyl)amino]benzoic acid benzyl ester.

Main reference materials

[1] (US5340801) Compounds having cholecystokinin and gastrin antagonistic properties