Reacción #2350960

ord-0f75f3bdb7dd420d83f6e3e8f71bab55

Ecuación de reacción

O=C(OCc1ccccc1)[C@H]1CCCN1Cc1cnc(NC(=O)N(C2CCCCC2)C2CCCCC2)s1
1-[2-(3,3-Dicyclohexyl-ureido)-thiazol-5-ylmethyl]-pyrrolidine-2(R)-carboxylic acid benzyl ester
→
O=C(O)[C@H]1CCCN1Cc1cnc(NC(=O)N(C2CCCCC2)C2CCCCC2)s1
pure acid
Rendimiento 84.8%
O=C(O)[C@H]1CCCN1Cc1cnc(NC(=O)N(C2CCCCC2)C2CCCCC2)s1
1-[2-(3,3-Dicyclohexyl-ureido)-thiazol-5-yl-methyl]-pyrrolidine-2(R)-carboxylic acid
Rendimiento 84.8%

Reactantes

O=C(OCc1ccccc1)[C@H]1CCCN1Cc1cnc(NC(=O)N(C2CCCCC2)C2CCCCC2)s1
1-[2-(3,3-Dicyclohexyl-ureido)-thiazol-5-ylmethyl]-pyrrolidine-2(R)-carboxylic acid benzyl ester

Reactivos

[Pd]
palladium on carbon

Disolventes

CO
MeOH

Condiciones de reacción

Condiciones detalladas
See reaction.notes.procedure_details.

Tratamiento posterior

  1. 1
    Otroto degas the mixture
  2. 2
    Otro(36 h)
  3. 3
    FiltraciónAfter filtering
  4. 4
    Concentraciónconcentration

Procedimiento

1-[2-(3,3-Dicyclohexyl-ureido)-thiazol-5-ylmethyl]-pyrrolidine-2(R)-carboxylic acid benzyl ester (50 mg, 0.095 mmol) was combined with palladium on carbon (25 mg) in MeOH. Vacuum was applied to degas the mixture. The reaction was subjected to hydrogen and vigorous stirring until no ester could be detected (36 h). After filtering and concentration, 35 mg (84%) pure acid was obtained by trituration.

Fuente

DOI: 10.6084/m9.figshare.5104873.v1Patente: US07851636B2uspto-grants-2010_12