Reacción #1269860

ord-be0401f095054d06816e3dd8a7157f51

Ecuación de reacción

CCCCOC(=O)N1CCN(C(=O)[C@H](CCC(=O)O)NC(=O)c2nc(-c3ccccc3)sc2/C=C/C(=O)O)CC1
suspension
CCCCOC(=O)N1CCN(C(=O)[C@H](CCC(=O)O)NC(=O)c2nc(-c3ccccc3)sc2/C=C/C(=O)O)CC1
4-((S)-4-Carboxy-2-{[5-((E)-2-carboxy-vinyl)-2-phenyl-thiazole-4-carbonyl]-amino}-butyryl)-piperazine-1-carboxylic acid butyl ester
CCCCOC(=O)N1CCN(C(=O)[C@H](CCC(=O)O)NC(=O)c2nc(-c3ccccc3)sc2CCC(=O)O)CC1
desired product
Rendimiento 33.8%
CCCCOC(=O)N1CCN(C(=O)[C@H](CCC(=O)O)NC(=O)c2nc(-c3ccccc3)sc2CCC(=O)O)CC1
4-((S)-4-Carboxy-2-{[5-(2-carboxy-ethyl)-2-phenyl-thiazole-4-carbonyl]-amino}-butyryl)-piperazine-1-carboxylic acid butyl ester
Rendimiento 33.8%

Disolventes

Condiciones de reacción

Condiciones detalladas
See reaction.notes.procedure_details.

Tratamiento posterior

  1. 1
    FiltraciónThe reaction mixture was filtrated over celite
  2. 2
    Otrothe filtrate evaporated to dryness

Procedimiento

A suspension of Example 19 (53 mg) and Pd/C (10%, 62 mg) in MeOH (2 mL) was stirred at RT under H2 atmosphere until reaction completion. The reaction mixture was filtrated over celite and the filtrate evaporated to dryness. Preparative HPLC (I) gave 18 mg of the desired product as yellow foam.

Fuente

DOI: 10.6084/m9.figshare.5104873.v1Patente: US08664203B2uspto-grants-2014_03