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

HRID 225105

Reaktionsgleichung

Reaktionsgleichung von HRID 225105
[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]

Komponenten

6

Edukt 2

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittel3×HCID 8028TetrahydrofuranLösungsmittelHCID 14798Sodium HydroxideLösungsmittel2×

Reaktionsbedingungen

Temperatur
5 °C

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-77124c5d3e0744a2860c4d0810547d56
Quelldatensatz
uspto-grants-1980_11
Patentnummer
US04235885

Verknüpfte Notizen

Wird geladen…