Reacción #944949

ord-ce5b54ae7f964ea1af3c30ceec69f09b

Ecuación de reacción

CC1CCN(C(=O)OC(C)(C)C)C1C(=O)O
tert-butoxycarbonyl-3-methyl-dl-proline
O=C(NCc1cc(Cl)ccc1-n1cnnn1)[C@@H]1CCCN1
N-[5-chloro-2-(1H-tetraazol-1-yl)benzyl]-L-prolinamide
→
CC1CCN(C(=O)OC(C)(C)C)[C@@H]1C(=O)N1CCC[C@H]1C(=O)NCc1cc(Cl)ccc1-n1cnnn1
title compound
CC1CCN(C(=O)OC(C)(C)C)[C@@H]1C(=O)N1CCC[C@H]1C(=O)NCc1cc(Cl)ccc1-n1cnnn1
1-(tert-butoxycarbonyl)-3-methylprolyl-N-[5-chloro-2-(1H-tetraazol-1-yl)benzyl]-L-prolinamide

Reactantes

CC1CCN(C(=O)OC(C)(C)C)C1C(=O)O
tert-butoxycarbonyl-3-methyl-dl-proline
O=C(NCc1cc(Cl)ccc1-n1cnnn1)[C@@H]1CCCN1
N-[5-chloro-2-(1H-tetraazol-1-yl)benzyl]-L-prolinamide

Reactivos

Ninguno

Disolventes

ClCCCl
EDC

Condiciones de reacción

Condiciones detalladas
See reaction.notes.procedure_details.

Tratamiento posterior

  1. 1
    OtroThe diastereomeric products were separated by reverse phase HPLC

Procedimiento

The title compound was prepared as a mixture of diastereomers from 1-(tert-butoxycarbonyl-3-methyl-dl-proline (16 mg, 0.07 mmol) and N-[5-chloro-2-(1H-tetraazol-1-yl)benzyl]-L-prolinamide (Example 26, Step B, 21 mg, 0.07 mmol), essentially according to the EDC coupling procedure described in Example 39, Step D. The diastereomeric products were separated by reverse phase HPLC and were carried on directly to deprotection.

Fuente

DOI: 10.6084/m9.figshare.5104873.v1Patente: US07144899B2uspto-grants-2006_12