反应详情

A solution of 0.48 g of ethyl 3-(N-tert.-butoxycarbonylamino)-2-(4-chlorophenyl)-2-hydroxy-propyl(diethoxymethyl)phosphinate in 10 ml of anhydrous dichloromethane is treated with 0.76 g of trimethylbromosilane and the resulting colourless solution stirred for 24 hours at room temperature under an inert atmosphere. The volatile materials are removed under reduced pressure to give a foam which is redisslued in 5 ml of methanol containing 1% of water and the solution stirred for 20 hours at room temperature. After this time evaporation of the solvent in vacuo followed by chromatography of the residue on reverse-phase silicagel and drying of the off white solid thus obtained in high vacuum gives 3-amino-2-(4-chlorophenyl)-2-hydroxypropyl(diethoxymethyl)phosphinic acid hydrobromide salt. Dissolution of the salt in the methanol and treatment with propylene oxide gives 3-amino-2-(4-chlorophenyl)-2-hydroxy-propyl(diethoxymethyl)phosphinic acid; 1H-NMR (D2O): δ(ppm)=7.39 (4H, m, Ph), 4.75 (1H, d, CH--P), 3.67-3.23 (6H, m, 2×CH2CO+CH 2 N), 2.38-1.97 (2H, ABq, CH2P), 1.23-1.04 (6H, t, 2×CH3).

1. customThe volatile materials are removed under reduced pressure
2. customto give a foam which
3. stirringthe solution stirred for 20 hours at room temperature
4. customAfter this time evaporation of the solvent in vacuo
5. customdrying of the off white solid
6. customthus obtained in high vacuum