Reacción #58021

Ecuación de reacción

DIPEA

PyBOP

(1-benzyloxycarbonylamino-2-methyl-propyl)-phosphonic acid monomethyl ester

5-tert-butoxycarbonylamino-2-hydroxy-pentanoic acid methyl ester

→

2-[(1-benzyloxycarbonylamino-2-methyl-propyl)-methoxy-phosphinoyloxy]-5-tert-butoxycarbonylamino-pentanoic acid methyl ester

Rendimiento 69.0%

Disolventes

Ethyl acetate

DMF

DMF

Condiciones de reacción

Tratamiento posterior

1. 1
   Lavadothe mixture was washed with 10% KHSO4
2. 2
   SecadoNaHCO3 and brine and dried
3. 3
   ConcentraciónConcentration under reduced pressure

Procedimiento

A solution of PyBOP (2.1 g, 4.0 mmol) in DMF (3 mL) was added to a mixture of (1-benzyloxycarbonylamino-2-methyl-propyl)-phosphonic acid monomethyl ester (1.0 g, 3.32 mmol) and 5-tert-butoxycarbonylamino-2-hydroxy-pentanoic acid methyl ester (865 mg, 3.5 mmol) in DMF (4 mL) under argon. DIPEA (2.28 mL, 13.3 mmol) was added dropwise and the mixture was stirred over night. Ethyl acetate was added and the mixture was washed with 10% KHSO4, satd. NaHCO3 and brine and dried. Concentration under reduced pressure followed by chromathography (heptane/EtOAc, 1:1→1:6) gave 2-[(1-benzyloxycarbonylamino-2-methyl-propyl)-methoxy-phosphinoyloxy]-5-tert-butoxycarbonylamino-pentanoic acid methyl ester (1.21 g, 69%).

Fuente