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

HRID 342260

反応式

HRID 342260 の反応式
[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

参加物

6

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-915f245d264f43d98f146b4733332d96
出典データセット
uspto-grants-1999_01
特許番号
US05856477

関連ノート

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