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Acetic Acid → Ethyl 3-(4-chlorobenzamido)-5-methyl-4-oxohexanoate

HRID 485018
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HRID 485018 반응식
[Cl:1][C:2]1[CH:16]=[CH:15][C:5]([C:6]([NH:8][CH2:9][C:10](=[O:14])[CH:11]([CH3:13])[CH3:12])=[O:7])=[CH:4][CH:3]=1.[H-].[Na+].Br[CH2:20][C:21]([O:23][CH2:24][CH3:25])=[O:22].C(O)(=O)C>CN(C)C=O.O>[Cl:1][C:2]1[CH:16]=[CH:15][C:5]([C:6]([NH:8][CH:9]([C:10](=[O:14])[CH:11]([CH3:13])[CH3:12])[CH2:20][C:21]([O:23][CH2:24][CH3:25])=[O:22])=[O:7])=[CH:4][CH:3]=1
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참가 물질

7

반응물 4

HCID 176Acetic AcidHCID 7748Ethyl bromoacetateHCID 24758Sodium hydrideHCID 134888004-Chloro-N-(3-methyl-2-oxobutyl)benzamide

생성물 1

HCID 13488801Ethyl 3-(4-chlorobenzamido)-5-methyl-4-oxohexanoate수율 92%

시약·촉매·용매 2

HCID 962Water
용매
HCID 6228Dimethylformamide용매

실험 절차

6 g of N-(4-chlorobenzoyl)isobutyrylmethylamine are dissolved in 30 ml of dimethylformamide, and 1.4 g of 61% sodium hydride are added thereto at -50° C. to -40° C. under stirring. When, 6.0 g of ethyl bromoacetate are added to the mixture at the same temperature. After the temperature of the mixture is risen to about 0° C. gradually, said mixture is further stirred until it becomes a clear solution. After the reaction, the mixture is neutralized with acetic acid, and then water is added thereto. The aqueous solution is extracted with ethyl acetate. The extract is washed with water, dried and then condensed under reduced pressure to remove solvent. The residue is recrystallized from a mixture of isopropyl ether and n-hexane. 7.5 g of ethyl 3-(4-chlorobenzoylamino)-3-isobutyrylpropionate are obtained. Yield: 92.0%.

후처리

  1. customis risen to about 0° C.
  2. stirringis further stirred until it
  3. customAfter the reaction
  4. extractionThe aqueous solution is extracted with ethyl acetate
  5. washThe extract is washed with water
  6. customdried
  7. customcondensed under reduced pressure
  8. customto remove solvent
  9. customThe residue is recrystallized from a mixture of isopropyl ether and n-hexane

출처 및 근거

ORD 기록
ord-696054164eb1485db6fcf3c4953300e1
출처 데이터셋
uspto-grants-1985_08
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US04535089

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