Reacción #217686

ord-78e22aa51b804b57ad0cb864cae78982

Ecuación de reacción

CCOC(=O)[C@@]1(N)[C@H]2[C@@H](C[C@H]1S(=O)(=O)Cc1ccc(Cl)c(Cl)c1)[C@]2(F)C(=O)OCC
(1R,2S,3R,5R,6R)-2-amino-3-(3,4-dichlorobenzylsulfonyl)-6-fluoro-bicyclo[3.1.0]hexane-2,6-dicarboxylic acid diethyl ester
[Na+].[OH-]
sodium hydroxide
→
N[C@]1(C(=O)O)[C@H]2[C@@H](C[C@H]1S(=O)(=O)Cc1ccc(Cl)c(Cl)c1)[C@]2(F)C(=O)O
(1R,2S,3R,5R,6R)-2-amino-3-(3,4-dichlorobenzylsulfonyl)-6-fluoro-bicyclo[3.1.0]hexane-2,6-dicarboxylic acid
Rendimiento 79.6%

Reactantes

CCOC(=O)[C@@]1(N)[C@H]2[C@@H](C[C@H]1S(=O)(=O)Cc1ccc(Cl)c(Cl)c1)[C@]2(F)C(=O)OCC
(1R,2S,3R,5R,6R)-2-amino-3-(3,4-dichlorobenzylsulfonyl)-6-fluoro-bicyclo[3.1.0]hexane-2,6-dicarboxylic acid diethyl ester
[Na+].[OH-]
sodium hydroxide

Reactivos

Ninguno

Disolventes

O=S(=O)(O)O
sulfuric acid

Condiciones de reacción

Condiciones detalladas
See reaction.notes.procedure_details.

Tratamiento posterior

  1. 1
    Temperaturacooled
  2. 2
    Otropurified by ion exchange resin (AG 50W-X8 Resin (H form), eluent

Procedimiento

108 mg of (1R,2S,3R,5R,6R)-2-amino-3-(3,4-dichlorobenzylsulfonyl)-6-fluoro-bicyclo[3.1.0]hexane-2,6-dicarboxylic acid diethyl ester was stirred in 1.08 mL of 60% sulfuric acid (W/V %) for 3 days at 130° C. The reaction solution was ice-cooled and then neutralized in an aqueous solution of 5N sodium hydroxide. The mixture was stirred for 1 hour at room temperature and then purified by ion exchange resin (AG 50W-X8 Resin (H form), eluent: water, a 30% aqueous solution of tetrahydrofuran and a 10% aqueous solution of pyridine), thereby yielding 76 mg of (1R,2S,3R,5R,6R)-2-amino-3-(3,4-dichlorobenzylsulfonyl)-6-fluoro-bicyclo[3.1.0]hexane-2,6-dicarboxylic acid.

Fuente

DOI: 10.6084/m9.figshare.5104873.v1Patente: US07381746B2uspto-grants-2008_06