Реакция #42685

ord-3ea9f59c3a734f2d85e5952b94dbcea4

Уравнение реакции

Cc1onc2c1C(=O)N=C(NC(=O)OC(C)(C)C)NCc1cc(Cl)c(c(Cl)c1)NC(=O)CN(C(=O)OC(C)(C)C)CC=CCOc1ccc-2cc1
intermediate
Cc1onc2c1C(=O)N=C(NC(=O)OC(C)(C)C)NCc1cc(Cl)c(c(Cl)c1)NC(=O)CN(C(=O)OC(C)(C)C)CC=CCOc1ccc-2cc1
tert-Butyl 9-((tert-butoxycarbonyl)amino)-14,30-dichloro-5-methyl-7,17-dioxo-4,24-dioxa-3,8,10,16,19-pentaazatetracyclo[23.2.2.212,15.02,6]-hentriaconta-1(27),2,5,8,12,14,21,25,28,30-decaene-19-carboxylate
O=C(O)C(F)(F)F
TFA
→
Cc1onc2c1C(=O)N=C(N)NCc1cc(Cl)c(c(Cl)c1)NC(=O)CNCC=CCOc1ccc-2cc1
title compound
Cc1onc2c1C(=O)N=C(N)NCc1cc(Cl)c(c(Cl)c1)NC(=O)CNCC=CCOc1ccc-2cc1
9-Amino-14,30-dichloro-5-methyl-4,24-dioxa-3,8,10,16,19-pentaazatetracyclo[23.2.2.212,15.02,6]hentriaconta-1(27),2,5,8,12,14,21,25,28,30-decaene-7,17-dione
O=C(O)C(F)(F)F
TFA

Реактанты

Cc1onc2c1C(=O)N=C(NC(=O)OC(C)(C)C)NCc1cc(Cl)c(c(Cl)c1)NC(=O)CN(C(=O)OC(C)(C)C)CC=CCOc1ccc-2cc1
intermediate
Cc1onc2c1C(=O)N=C(NC(=O)OC(C)(C)C)NCc1cc(Cl)c(c(Cl)c1)NC(=O)CN(C(=O)OC(C)(C)C)CC=CCOc1ccc-2cc1
tert-Butyl 9-((tert-butoxycarbonyl)amino)-14,30-dichloro-5-methyl-7,17-dioxo-4,24-dioxa-3,8,10,16,19-pentaazatetracyclo[23.2.2.212,15.02,6]-hentriaconta-1(27),2,5,8,12,14,21,25,28,30-decaene-19-carboxylate
O=C(O)C(F)(F)F
TFA

Реагенты

Нет

Растворители

ClCCl
DCM

Условия реакции

Подробные условия
See reaction.notes.procedure_details.

Обработка

  1. 1
    ДругоеTFA and DCM were evaporated in vacuo
  2. 2
    Другоеto give a crude product, which
  3. 3
    Другоеwas purified by preparative HPLC

Методика

The intermediate (24 mg) from Step 1(C) was dissolved in 2 mL of TFA and DCM mixture (1:1). The resulted solution was stirred at room temperature for 1 h. TFA and DCM were evaporated in vacuo to give a crude product, which was purified by preparative HPLC to give the title compound as a TFA salt (19.9 mg).

Источник

DOI: 10.6084/m9.figshare.5104873.v1Патент: US07732434B2uspto-grants-2010_06