2-Bromo-1-(5-chloro-2-methoxyphenyl)ethanone → 5-[4-(5-Chloro-2-methoxy-phenyl)-oxazol-2-yl]-pentanoic acid methyl ester

HRID 1443740Notes

Reaction equation

HRID 1443740 reaction equation
Br[CH2:2][C:3]([C:5]1[CH:10]=[C:9]([Cl:11])[CH:8]=[CH:7][C:6]=1[O:12][CH3:13])=O.[CH3:14][O:15][C:16](=[O:24])[CH2:17][CH2:18][CH2:19][CH2:20][C:21](=[O:23])[NH2:22]>CO>[CH3:14][O:15][C:16](=[O:24])[CH2:17][CH2:18][CH2:19][CH2:20][C:21]1[O:23][CH:2]=[C:3]([C:5]2[CH:10]=[C:9]([Cl:11])[CH:8]=[CH:7][C:6]=2[O:12][CH3:13])[N:22]=1

Participants

4

Reactant 2

HCID 19891882-Bromo-1-(5-chloro-2-methoxyphenyl)ethanoneHCID 14266897Methyl 6-amino-6-oxohexanoate

Product 1

HCID 591677715-[4-(5-Chloro-2-methoxy-phenyl)-oxazol-2-yl]-pentanoic acid methyl ester

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Combine 2-bromo-1-(5-chloro-2-methoxy-phenyl)-ethanone (12.0 g, 46 mmol) with 5-carbamoyl-pentanoic acid methyl ester (12.7 g, 79.9 mmol) and heat the neat mixture in a sealed vessel at 120-140° C. for about 6 h. Cool the mixture and add methanol and allow the mixture to stir overnight at room temperature. Concentrate the mixture and partition the residue between aq NaHCO3 and EtOAc. Dry the combined extracts over Na2SO4 and concentrate. Chromatography over silica gel (CHCl3) allows for recovery of 5-[4-(5-chloro-2-methoxy-phenyl)-oxazol-2-yl]-pentanoic acid methyl ester (5.5 g, 37%). MS (ES): (M+1)+ 324.1, 326.1 m/z.

Workup

  1. temperatureCool the mixture
  2. concentrationConcentrate the mixture
  3. custompartition the residue between aq NaHCO3 and EtOAc
  4. dry with materialDry the combined extracts over Na2SO4
  5. concentrationconcentrate

Sources & evidence

ORD record
ord-aa0f24bd5c684ecaa1c29a2aa1d179ea
Source dataset
uspto-grants-2010_02
Patent number
US07662771B2

Reaction notes

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