碘甲烷 → (S)-2-Phthalimido-6-hydroxyhexanoic acid, methyl ester

HRID 1198

反应方程式

HRID 1198 反应方程式
[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

参与物

6

反应物 3

HCID 6328碘甲烷HCID 10796碳酸氢铯HCID 11065730(S)-2-Phthalimido-6-hydroxyhexanoic acid

产物 1

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

试剂、催化剂与溶剂 2

HCID 6228N,N-二甲基甲酰胺溶剂HCID 8857乙酸乙酯溶剂

实验过程

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.

后处理

  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

来源与证据

ORD记录
ord-efe923230555472e8f595617781b5290
来源数据集
uspto-grants-1998_03
专利号
US05723457

关联笔记

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