Ethyl bromoacetate → HCID 69289974, compound

HRID 1247256Notes

Reaction equation

HRID 1247256 reaction equation
[C:1]([C:3]1[CH:25]=[CH:24][C:6]([CH2:7][NH:8][C:9](=[O:23])[CH:10]([O:20][CH2:21][CH3:22])[C:11]2[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[C:13]([OH:19])[CH:12]=2)=[CH:5][CH:4]=1)#[N:2].C([O-])([O-])=O.[K+].[K+].Br[CH2:33][C:34]([O:36][CH2:37][CH3:38])=[O:35]>CN(C=O)C.CCOC(C)=O>[CH2:37]([O:36][C:34](=[O:35])[CH2:33][O:19][C:13]1[CH:12]=[C:11]([CH:10]([C:9](=[O:23])[NH:8][CH2:7][C:6]2[CH:5]=[CH:4][C:3]([C:1]#[N:2])=[CH:25][CH:24]=2)[O:20][CH2:21][CH3:22])[CH:16]=[CH:15][C:14]=1[O:17][CH3:18])[CH3:38]

Participants

6

Reactant 3

HCID 7748Ethyl bromoacetateHCID 11430Potassium CarbonateHCID 21905604HCID 21905604, compound

Product 1

HCID 69289974HCID 69289974, compoundYield 80.8%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a stirred solution of (RS)-N-(4-cyano-benzyl)-2-ethoxy-2-(3-hydroxy-4-methoxy-phenyl)-acetamide (0.158 g) at rt in DMF (1.5 ml) were added K2CO3 (0.067 g) and ethyl bromoacetate (0.081 g). The reaction mixture was then stirred at rt under an argon atmosphere for 24 h. The mixture was diluted with EtOAc (10 ml), washed with water (10 ml+10 ml) and brine (10 ml), dried (MgSO4), filtered and concentrated (rotavapor). The product was purified by chromatography (Silicagel (20 g) using a gradient profile: cyclohexane to cyclohexane/EtOAc 45:55) to give (RS)-{5-[(4-cyano-benzylcarbamoyl)-ethoxy-methyl]-2-methoxy-phenoxy}-acetic acid ethyl ester (0.160 g) as a colorless gum.

Workup

  1. washwashed with water (10 ml+10 ml) and brine (10 ml)
  2. dry with materialdried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated (rotavapor)
  5. customThe product was purified by chromatography (Silicagel (20 g)

Sources & evidence

ORD record
ord-a36306b49d8f40758b57a815282b121a
Source dataset
uspto-grants-2006_10
Patent number
US07129238B2

Reaction notes

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