Phenol → HCID 68718986, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of ((R)-3-tert-butoxycarbonylamino-2-hydroxy-propyl)-cyclohexylmethyl-phosphinic acid (0.67 g, 2.0 mmol) in 10 mL THF at 0° C. was added 1-chloro-N, N-2-trimethyl-1-propenylamine (319 mg, 2.4 mmol). After stirring for 10 min at 0° C., a solution of phenol (188 mg, 2.0 mmol) and triethylamine (243 mg, 2.4 mmol) in THF (3 mL) was added dropwise. After addition the reaction mixture was stirred at 0° C. for 2 h and then room temperature for 16 h. The reaction was diluted with ethyl acetate and washed with water and brine. The organic layer was dried with magnesium sulfate, filtered and concentrated in vacuo to give the crude product. Purification by gradient flash chromatography (methanol/methylene chloride) on a 35 g RediSep disposable column gave ((R)-3-tert-butoxycarbonylamino-2-hydroxy-propyl)-cyclohexylmethyl-phosphinic acid phenyl ester (500 mg, 1.22 mmol). 1H-NMR (CDCl3, 300 MHz): δ 7.35 (m, 2H), 7.18 (m, 3H), 4.18 (br s, H), −33.21-3.09 (m, 2H), 2.01-1.58 (m, 10H), 1.43-0.95 (m, 15H). 31P NMR (CD3OD, 300 MHz): 57.90, 58.65.

Provenance & Evidence