Реакция #58021

Уравнение реакции

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

Выход 69.0%

Растворители

Ethyl acetate

DMF

DMF

Условия реакции

Обработка

1. 1
   Промывкаthe mixture was washed with 10% KHSO4
2. 2
   СушкаNaHCO3 and brine and dried
3. 3
   КонцентрированиеConcentration under reduced pressure

Методика

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%).

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