Overview[1]
1-Naphthyl dichlorophosphate is an ester compound and can be used as a pharmaceutical synthesis intermediate.
Preparation[1]
1-Naphthyl dichlorophosphate is prepared as follows: from 1-naphthol (3.00g, 20.81mmol), phosphorus oxychloride (1.94mL, 20.81mmol), triethylamine (2.9mL, 20.81mmol) and anhydrous Diethyl ether (70 mL) was prepared. After 1 hour at -78°C, the reaction was allowed to warm to room temperature and stirred for 3 hours. The crude product was obtained as an oil. The resulting mixture was filtered and evaporated in vacuo to give 1-naphthyl dichlorophosphate (4.59 g, 84) as a colorless oil after purification by column chromatography eluting with hexane-EtOAc (1:1). [Rf=0.93 (hexane-EtOAc, 1:1)], 31PNMR (202MHz, CDCl3): δP5.07; 1HNMR (500MHz, CDCl3): δH7.52-7.71 (m, 4H, ArH), 7.86-7.89 (m, 1H, ArH), 7.95-7.98 (m, 1H, ArH), 8.16-8.19 (m, 1H, ArH).
Apply[1]
1-Naphthyl dichlorophosphate can be used as a pharmaceutical synthesis intermediate. To prepare 1-naphthyl(benzyl-L-alanyl)chlorophosphate: under an argon atmosphere at -78°C, use 1-naphthyl dichlorophosphate (2.50g, 9.57mmol), L- Alanine benzyl ester tosylate (3.36g, 9.57mmol), anhydrous triethylamine (2.66mL, 19 antioxidant 4020.14mmol) and anhydrous dichloromethane (35.7mL). After 1 hour, the reaction mixture was slowly warmed to room temperature for 3 hours and the formation of the desired compound was monitored by 31 PNMR. The reaction mixture was concentrated under reduced pressure under nitrogen, the residue was redissolved in diethyl ether, filtered and evaporated in vacuo to give a crude colorless oil, which in some cases was used without further purification below One step. The synthesized aryl chlorophosphate was purified by column chromatography eluting with hexane-EtOAc (7:3) to give the title compound as a colorless oil. 1HNMR (500MHz, CDCl3, mixture of diastereomers in a ratio of 1:1): δH1.42-1.45 (m, 3H, CHCH3), 4.20-4.23 (m, 1H, CHCH3), 4.78-4.81 ( m, 1H, NH), 5.09 (s, 2H, OCH2Ph), 7.09-7.73 (m, 11H, Ar aqueous amino resin H), 7.97-8.12 (m, 1H, ArH).
