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

HRID 225106

반응식

HRID 225106 반응식
[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]

참가 물질

7

반응물 3

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

생성물 1

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

시약·촉매·용매 3

HCID 962Water용매2회HCID 8028Tetrahydrofuran용매2회HCID 14798Sodium Hydroxide용매2회

반응 조건

온도
5 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-5b7717d8116b45ec806aa6dd8478d922
출처 데이터셋
uspto-grants-1980_11
특허 번호
US04235885

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