Ethyl bromoacetate → HCID 20271337, compound

HRID 485026Notes

Reaction equation

HRID 485026 reaction equation
[F:1][C:2]1[CH:17]=[CH:16][C:5]([C:6]([NH:8][CH2:9][C:10](=[O:15])[CH2:11][CH:12]([CH3:14])[CH3:13])=[O:7])=[CH:4][CH:3]=1.[OH-].[K+].Br[CH2:21][C:22]([O:24][CH2:25][CH3:26])=[O:23]>CS(C)=O>[F:1][C:2]1[CH:17]=[CH:16][C:5]([C:6]([NH:8][CH:9]([C:10](=[O:15])[CH2:11][CH:12]([CH3:14])[CH3:13])[CH2:21][C:22]([O:24][CH2:25][CH3:26])=[O:23])=[O:7])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 7748Ethyl bromoacetateHCID 14797Potassium HydroxideHCID 134903084-Fluoro-N-(4-methyl-2-oxopentyl)benzamide

Product 1

HCID 20271337HCID 20271337, compoundYield 64.8%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

4.0 g of N-(4-fluorobenzoyl)isovalerylmethylamine are dissolved in 20 ml of dimethylsulfoxide and 1.3 g of potassium hydroxide are added thereto at 5° C. to 10° C. under vigorous stirring. The mixture is further stirred for 10 minutes. 3.1 g of ethyl bromoacetate are added dropwise to the mixture at the same temperature, and said mixture is further stirred for 2 hours. After the reaction, the mixture is treated in the same manner as described in Preparation 1-(5). 3.5 g of ethyl 3-(4-fluorobenzoylamino)-3-isovalerylpropionate are thereby obtained as oil. Yield: 64.8%.

Workup

  1. customat 5° C. to 10° C.
  2. stirringis further stirred for 2 hours
  3. customAfter the reaction
  4. additionthe mixture is treated in the same manner
  5. customas described in Preparation 1-(5)

Sources & evidence

ORD record
ord-df7d097f90fd48049965a8e0143d6d27
Source dataset
uspto-grants-1985_08
Patent number
US04535089

Reaction notes

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