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

HRID 1039242Notes

Reaction equation

HRID 1039242 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-3f61906a890a4ffdb08e47addacbf278
Source dataset
uspto-grants-2013_10
Patent number
US08552039B2

Reaction notes

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