Toluene → 8-[[2-(Chloromethyl)-4-methyl-1-oxopentyl]amino]octanoic acid

HRID 225106

Reaktionsgleichung

Reaktionsgleichung von HRID 225106
[NH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][C:9]([OH:11])=[O:10].C1(C)C=CC=CC=1.[Cl:19][CH2:20][CH:21]([CH2:25][CH:26]([CH3:28])[CH3:27])[C:22](Cl)=[O:23]>O.[OH-].[Na+].C1COCC1>[Cl:19][CH2:20][CH:21]([CH2:25][CH:26]([CH3:28])[CH3:27])[C:22]([NH:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][C:9]([OH:11])=[O:10])=[O:23]

Komponenten

7

Edukt 3

HCID 1140TolueneHCID 660858-Aminooctanoic acidHCID 127690672-(Chloromethyl)-4-methylvaleryl chloride

Produkt 1

HCID 205639668-[[2-(Chloromethyl)-4-methyl-1-oxopentyl]amino]octanoic acid

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittel2×HCID 8028TetrahydrofuranLösungsmittel2×HCID 14798Sodium HydroxideLösungsmittel2×

Reaktionsbedingungen

Temperatur
5 °C

Versuchsvorschrift

8-Amino caprylic acid (4.3 g) is dissolved in 20 ml of water containing 1.1 g of sodium hydroxide. To this is added 20 ml of THF, and 5 ml of toluene, and the solution is cooled to 5° C. 2-(Chloromethyl)-4-methylvaleryl chloride is dissolved in 10 ml of THF and added dropwise to the above solution. The pH of the reaction mixture is maintained between 8 and 9 during the reaction time by the addition of a total of 1.1 g of sodium hydroxide in 20 ml of water, as needed. After stirring at room temperature for about 16 hours, the aqueous layer is separated and acidified with 10% hydrochloric acid. Product is extracted with ethyl acetate and the ethyl acetate is dried with magnesium sulfate, filtered and concentrated in vacuo to yield 5.6 g of product.

Aufarbeitung

  1. additionadded dropwise to the above solution
  2. customthe aqueous layer is separated
  3. extractionProduct is extracted with ethyl acetate
  4. dry with materialthe ethyl acetate is dried with magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-5b7717d8116b45ec806aa6dd8478d922
Quelldatensatz
uspto-grants-1980_11
Patentnummer
US04235885

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