Reacción #41503

ord-763b9194fd804b829a1dc772f17f5c7c

Ecuación de reacción

COc1cc([C@@H](O)C(C)NC(=O)OC(C)(C)C)ccc1SC
t-Butyl (R)-1-hydroxy-1-(3-methoxy-4-(methylthio)phenyl)propan-2-ylcarbamate
→
COc1cc([C@@H](O)[C@@H](C)N)ccc1SC
(1R,2R)-2-amino-1-(3-methoxy-4-(methylthio)phenyl)propan-1-ol

Reactantes

COc1cc([C@@H](O)C(C)NC(=O)OC(C)(C)C)ccc1SC
t-Butyl (R)-1-hydroxy-1-(3-methoxy-4-(methylthio)phenyl)propan-2-ylcarbamate

Reactivos

Ninguno

Disolventes

CCOC(C)=O
ethyl acetate

Condiciones de reacción

Temperatura
60°CELSIUS
Condiciones detalladas
See reaction.notes.procedure_details.

Tratamiento posterior

  1. 1
    OtroThe solvent was evaporated
  2. 2
    Otrothe diastereomers were separated by HPLC (XBridge column)

Procedimiento

t-Butyl (R)-1-hydroxy-1-(3-methoxy-4-(methylthio)phenyl)propan-2-ylcarbamate (308c, 44 μg, 130 μmol) was dissolved in a solution of HC in ethyl acetate (1M, 5 mL) and stirred at 60° C. for 2 h. The solvent was evaporated, and the diastereomers were separated by HPLC (XBridge column). The subtitle compound is the first eluted product, 17 mg (55%).

Fuente

DOI: 10.6084/m9.figshare.5104873.v1Patente: US07728030B2uspto-grants-2010_06