Reaktion #58021

Reaktionsgleichung

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

Ausbeute 69.0%

Lösungsmittel

Ethyl acetate

DMF

DMF

Reaktionsbedingungen

Aufarbeitung

1. 1
   Waschenthe mixture was washed with 10% KHSO4
2. 2
   TrocknenNaHCO3 and brine and dried
3. 3
   EinengenConcentration under reduced pressure

Vorschrift

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%).

Quelle