Реакция #467416

ord-62fb668c509940d7b350e2f074a35e7c

Уравнение реакции

COC(=O)N[C@H](C(=O)N[C@@H](Cc1ccccc1)[C@@H](O)CN(N)Cc1ccc(-c2ccccn2)cc1)C(C)(C)C.Cl
1-[4-(pyridin-2-yl)-phenyl]-4(S)-hydroxy-2-amino-5(S)-N-(N-methoxycarbonyl-(L)-tert-leucyl)amino-6-phenyl-2-azahexane hydrochloride
COC(=O)N[C@H](C(=O)O)C(C)C
N-methoxycarbonyl-(L)-valine
ClCCCl
EDC
On1nnc2ccccc21
HOBT
CN(C)C=O
DMF
CN(C)C=O
DMF
→
CON[C@H](C(=O)NN(Cc1ccc(-c2ccccn2)cc1)C[C@H](O)[C@H](Cc1ccccc1)NC(=O)[C@@H](NC(=O)OC)C(C)(C)C)C(C)C=C=O
title compound
CON[C@H](C(=O)NN(Cc1ccc(-c2ccccn2)cc1)C[C@H](O)[C@H](Cc1ccccc1)NC(=O)[C@@H](NC(=O)OC)C(C)(C)C)C(C)C=C=O
1-[4-(Pyridin-2-yl)-phenyl]-4(S)-hydroxy-2-N-(N-methoxy-carbonyl-(L)-valyl)amino-5(S)-N-(N-methoxycarbonyl-(L)-tert-leucyl)amino-6-phenyl-2-azahexane

Реактанты

—
crude product
—
TEA
COC(=O)N[C@H](C(=O)N[C@@H](Cc1ccccc1)[C@@H](O)CN(N)Cc1ccc(-c2ccccn2)cc1)C(C)(C)C.Cl
1-[4-(pyridin-2-yl)-phenyl]-4(S)-hydroxy-2-amino-5(S)-N-(N-methoxycarbonyl-(L)-tert-leucyl)amino-6-phenyl-2-azahexane hydrochloride
COC(=O)N[C@H](C(=O)O)C(C)C
N-methoxycarbonyl-(L)-valine
ClCCCl
EDC
On1nnc2ccccc21
HOBT
CN(C)C=O
DMF
CN(C)C=O
DMF

Реагенты

Нет

Условия реакции

Подробные условия
See reaction.notes.procedure_details.

Обработка

  1. 1
    Фильтрацияfiltered off
  2. 2
    Другоеdried

Методика

Analogously to Example 1, a solution of 0.964 g (1.5 mmol) of 1-[4-(pyridin-2-yl)-phenyl]-4(S)-hydroxy-2-amino-5(S)-N-(N-methoxycarbonyl-(L)-tert-leucyl)amino-6-phenyl-2-azahexane hydrochloride in 10 ml of DMF is added dropwise to a mixture of 0.42 g (2.4 mmol) of N-methoxycarbonyl-(L)-valine, 0.862 g (4.5 mmol) of EDC, 0.405 g (3 mmol) of HOBT and 1.26 ml of TEA in 10 ml of DMF. After working up, the crude product is digested in DIPE, filtered off and dried. Subsequent column chromatography (SiO2; hexane/ethyl acetate: 1/1 to 3/1) yields the pure title compound (TLC: Rf=0.35 (ethyl acetate); HPLC20-100: tRet=10.9. FAB MS (M+H)+=691.

Источник

DOI: 10.6084/m9.figshare.5104873.v1Патент: US06300519B1uspto-grants-2001_10