반응 #58021

반응 방정식

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

수율 69.0%

용매

Ethyl acetate

DMF

DMF

반응 조건

후처리

1. 1
   세척the mixture was washed with 10% KHSO4
2. 2
   건조NaHCO3 and brine and dried
3. 3
   농축Concentration under reduced pressure

실험 절차

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%).

출처