Reacción #1430

ord-42ed6fb7dd91419caecfec4b1a99a601

Ecuación de reacción

O=C(O)[C@H](CCCCO)N1C(=O)c2ccccc2C1=O
(S)-2-phthalimido-6-hydroxyhexanoic acid
O=C([O-])[O-].[Cs+].[Cs+]
cesium carbonate
CI
methyl iodide
COC(=O)[C@H](CCCCO)N1C(=O)c2ccccc2C1=O
title product
Rendimiento 196.0%
COC(=O)[C@H](CCCCO)N1C(=O)c2ccccc2C1=O
(S)-2-Phthalimido-6-hydroxyhexanoic acid, methyl ester
Rendimiento 196.0%

Condiciones de reacción

Condiciones detalladas
See reaction.notes.procedure_details.

Tratamiento posterior

  1. 1
    Lavadowashed successively with water containing a small amount of sodium bisulfite, water, 50% saturated sodium bicarbonate, and brine
  2. 2
    Secadodried (sodium sulfate)
  3. 3
    Filtraciónfiltered

Procedimiento

A slurry of (S)-2-phthalimido-6-hydroxyhexanoic acid (3.752 g., 13.5 mmol.) and cesium carbonate (2.178 g., 6.7 mmol.) in dimethylformamide (44 ml.) was treated with methyl iodide (3.0 ml., 6.84 g., 48.2 mmol.). After stirring at room temperature for 2 hours, the mixture was diluted with ethyl acetate and washed successively with water containing a small amount of sodium bisulfite, water, 50% saturated sodium bicarbonate, and brine, then dried (sodium sulfate), filtered and stripped to give the title product as a colorless oil (3.825 g.). The oil was homogeneous by

Fuente

DOI: 10.6084/m9.figshare.5104873.v1Patente: US05723602uspto-grants-1998_03