1,3-Diethyl 2-oxopropanedioate → HCID 54166445, compound

HRID 1032531Notes

Reaction equation

HRID 1032531 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][NH:10][C:11](=[O:16])[C:12]([F:15])([F:14])[F:13])=[CH:4][C:3]=1[O:17][CH3:18].[CH2:19]([O:21][C:22](=[O:30])[C:23]([C:25](OCC)=[O:26])=[O:24])[CH3:20]>C(O)(=O)C>[CH2:19]([O:21][C:22]([C:23]1([OH:24])[C:7]2[C:2](=[C:3]([O:17][CH3:18])[CH:4]=[C:5]([CH2:8][CH2:9][NH:10][C:11](=[O:16])[C:12]([F:14])([F:15])[F:13])[CH:6]=2)[NH:1][C:25]1=[O:26])=[O:30])[CH3:20]

Participants

4

Reactant 2

HCID 691051,3-Diethyl 2-oxopropanedioateHCID 22165979HCID 22165979, compound

Product 1

HCID 54166445HCID 54166445, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

2.5 g of N-[2-(4-amino-3-methoxyphenyl)ethyl]trifluoroacetamide and 1.9 ml of mesoxalic acid diethyl ester are dissolved in 25 ml of acetic acid and refluxed for 4 hours. The mixture is concentrated, the residue dissolved in ethyl acetate and extracted twice by shaking with saturated sodium bicarbonate solution. The mixture is concentrated and chromatographed on silica gel with cyclohexane/ethyl acetate 1:1, thus obtaining 2.5 g of 2,3-dihydro-3-hydroxy-7-methoxy-2-oxo-5-(trifluoroacetamidoethyl)-3-indolecarboxylic acid ethyl ester, mp 115°-117° C.

Workup

  1. temperaturerefluxed for 4 hours
  2. concentrationThe mixture is concentrated
  3. dissolutionthe residue dissolved in ethyl acetate
  4. extractionextracted twice
  5. concentrationThe mixture is concentrated
  6. customchromatographed on silica gel with cyclohexane/ethyl acetate 1:1

Sources & evidence

ORD record
ord-f7dd475d04f94e5eb74413984708684b
Source dataset
uspto-grants-1990_09
Patent number
US04958026

Reaction notes

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