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

HRID 485018Notes

Reaction equation

HRID 485018 reaction equation
[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

Participants

7

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

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%.

Workup

  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

Sources & evidence

ORD record
ord-696054164eb1485db6fcf3c4953300e1
Source dataset
uspto-grants-1985_08
Patent number
US04535089

Reaction notes

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