Methyl iodide → (S)-2-Phthalimido-6-hydroxyhexanoic acid, methyl ester

HRID 2256450

Reaction equation

HRID 2256450 reaction equation
[C:1]1(=[O:20])[N:5]([C@@H:6]([CH2:10][CH2:11][CH2:12][CH2:13][OH:14])[C:7]([OH:9])=[O:8])[C:4](=[O:15])[C:3]2=[CH:16][CH:17]=[CH:18][CH:19]=[C:2]12.[C:21](=O)([O-])[O-].[Cs+].[Cs+].CI>CN(C)C=O.C(OCC)(=O)C>[C:4]1(=[O:15])[N:5]([C@@H:6]([CH2:10][CH2:11][CH2:12][CH2:13][OH:14])[C:7]([O:9][CH3:21])=[O:8])[C:1](=[O:20])[C:2]2=[CH:19][CH:18]=[CH:17][CH:16]=[C:3]12

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 10796Cesium carbonateHCID 11065730(S)-2-Phthalimido-6-hydroxyhexanoic acid

Product 1

HCID 10859253(S)-2-Phthalimido-6-hydroxyhexanoic acid, methyl esterYield 196%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

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 TLC (1:1-acetone:hexanes) Rf =0.37.

Workup

  1. washwashed successively with water containing a small amount of sodium bisulfite, water, 50% saturated sodium bicarbonate, and brine
  2. dry with materialdried (sodium sulfate)
  3. filtrationfiltered

Sources & evidence

ORD record
ord-d42514b9d49944c788fa12e6bc81e4a0
Source dataset
uspto-grants-1997_08
Patent number
US05654294

Linked notes

Loading…