Реакция #81114

ord-edd996bb594048adbf6145cfa7f2e7cb

Уравнение реакции

CC(C)[C@H](NC(=O)CBr)C(=O)NC(Cc1ccccc1)C(O)C(O)C(Cc1ccccc1)NC(=O)[C@@H](NC(=O)CBr)C(C)C
resultant compound
CC(C)[C@H](NC(=O)CBr)C(=O)NC(Cc1ccccc1)C(O)C(O)C(Cc1ccccc1)NC(=O)[C@@H](NC(=O)CBr)C(C)C
2,5-Di-{N-Bromoacetyl-(L)-Valyl}amino-3,4-dihydroxy-1,6-diphenyl hexane
Sc1ncc[nH]1
2-mercaptoimidazole
→
CC(C)[C@H](NC(=O)CSc1ncc[nH]1)C(=O)NC(Cc1ccccc1)C(O)C(O)C(Cc1ccccc1)NC(=O)[C@@H](NC(=O)CSc1ncc[nH]1)C(C)C
title compound
Выход 47.5%
CC(C)[C@H](NC(=O)CSc1ncc[nH]1)C(=O)NC(Cc1ccccc1)C(O)C(O)C(Cc1ccccc1)NC(=O)[C@@H](NC(=O)CSc1ncc[nH]1)C(C)C
2,5-Di-{N-[(Imidazol-2-yl)-thiomethylcarbonyl]-(L)-Valyl}amino-3,4-dihydroxy-1,6-diphenyl hexane
Выход 47.5%

Реактанты

CC(C)[C@H](NC(=O)CBr)C(=O)NC(Cc1ccccc1)C(O)C(O)C(Cc1ccccc1)NC(=O)[C@@H](NC(=O)CBr)C(C)C
resultant compound
CC(C)[C@H](NC(=O)CBr)C(=O)NC(Cc1ccccc1)C(O)C(O)C(Cc1ccccc1)NC(=O)[C@@H](NC(=O)CBr)C(C)C
2,5-Di-{N-Bromoacetyl-(L)-Valyl}amino-3,4-dihydroxy-1,6-diphenyl hexane
Sc1ncc[nH]1
2-mercaptoimidazole

Реагенты

Нет

Условия реакции

Подробные условия
See reaction.notes.procedure_details.

Обработка

  1. 1
    Другоеsimilarly purified

Методика

The resultant compound of Example 251 (150 mg, 0.2 mmol) was reacted with 2-mercaptoimidazole (40.6 mg) by the procedure described in Example 252 and similarly purified to afford the title compound (74 mg, 47%). 1H NMR (DMSO-d6, 300 MHz) δ 0.63 (m, 12H), 1.84 (m, 2H), 2.25-2.80 (m, 4H), 3.05-3.82 (m, 12H), 4.44 (m, 2H), 7.14 (m, 14H), 7.48 (bd, 2H), 8.07 (bd, 2H). MS (FAB) m/e 779 (M+H)+.

Источник

DOI: 10.6084/m9.figshare.5104873.v1Патент: US05616714uspto-grants-1997_04