5-Aminovaleric acid → 5-[[2-(Chloromethyl)-4-methyl-1-oxopentyl]amino]pentanoic acid

HRID 225105

反応式

HRID 225105 の反応式
[NH2:1][CH2:2][CH2:3][CH2:4][CH2:5][C:6]([OH:8])=[O:7].[Cl:9][CH2:10][CH:11]([CH2:15][CH:16]([CH3:18])[CH3:17])[C:12](Cl)=[O:13]>O.[OH-].[Na+].C1COCC1>[Cl:9][CH2:10][CH:11]([CH2:15][CH:16]([CH3:18])[CH3:17])[C:12]([NH:1][CH2:2][CH2:3][CH2:4][CH2:5][C:6]([OH:8])=[O:7])=[O:13]

参加物

6

反応物 2

HCID 1385-Aminovaleric acidHCID 127690672-(Chloromethyl)-4-methylvaleryl chloride

生成物 1

HCID 205639675-[[2-(Chloromethyl)-4-methyl-1-oxopentyl]amino]pentanoic acid

試薬・触媒・溶媒 3

HCID 962Water溶媒3 回HCID 8028Tetrahydrofuran溶媒HCID 14798Sodium Hydroxide溶媒2 回

反応条件

温度
5 °C

実験手順

5-Aminovaleric acid (3.2 g) is dissolved in 15 ml of water containing 1.09 g of sodium hydroxide. This is cooled to 5° C. and 2-(chloromethyl)-4-methylvaleryl chloride in 30 ml of THF is added dropwise. The pH is maintained at 8-9 by the dropwise addition of 1.09 g sodium hydroxide in 20 ml of water as needed. After stirring for about 16 hours the reaction mixture is diluted with 30 ml of water and concentrated in vacuo to remove THF. The aqueous layer is washed with ether, and acidified with 10% hydrochloric acid. Product is extracted with ethyl acetate. The ethyl acetate is dried with magnesium sulfate, filtered and concentrated in vacuo to yield 4.3 g of product. Product is purified by the solvent system 500 parts ether: 10 parts methanol: 5 parts acetic acid, yielding 2.0 g of material.

後処理

  1. concentrationconcentrated in vacuo
  2. customto remove THF
  3. washThe aqueous layer is washed with ether
  4. extractionProduct is extracted with ethyl acetate
  5. dry with materialThe ethyl acetate is dried with magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-77124c5d3e0744a2860c4d0810547d56
出典データセット
uspto-grants-1980_11
特許番号
US04235885

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