2-Bromo-1-[2-(trifluoromethyl)phenyl]ethan-1-one → 5-[4-(2-Trifluoromethyl-phenyl)-oxazol-2-yl]-pentanoic acid methyl ester

HRID 1039254Notes

Reaction equation

HRID 1039254 reaction equation
Br[CH2:2][C:3]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[C:11]([F:14])([F:13])[F:12])=O.[CH3:15][O:16][C:17](=[O:25])[CH2:18][CH2:19][CH2:20][CH2:21][C:22](=[O:24])[NH2:23]>O>[CH3:15][O:16][C:17](=[O:25])[CH2:18][CH2:19][CH2:20][CH2:21][C:22]1[O:24][CH:2]=[C:3]([C:5]2[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=2[C:11]([F:14])([F:13])[F:12])[N:23]=1

Participants

4

Reactant 2

HCID 27784302-Bromo-1-[2-(trifluoromethyl)phenyl]ethan-1-oneHCID 14266897Methyl 6-amino-6-oxohexanoate

Product 1

HCID 591677795-[4-(2-Trifluoromethyl-phenyl)-oxazol-2-yl]-pentanoic acid methyl ester

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Combine 2-bromo-1-(2-trifluoromethyl-phenyl)-ethanone (6.6 g, 24.7 mmol) with 5-carbamoyl-pentanoic acid methyl ester (7.8 g, 49 mmol) and heat the neat mixture in a sealed vessel at 140-150° C. for about 4.5 hours. Cool the mixture, dilute with water, and extract with EtOAc. Dry the combined extracts over Na2SO4 and concentrate. Chromatography over silica gel (CH2Cl2) allows for recovery of 5-[4-(2-trifluoromethyl-phenyl)-oxazol-2-yl]-pentanoic acid methyl ester (3.47 g, 43%). MS (ES): (M+1)+ 328.2 m/z.

Workup

  1. temperatureCool the mixture
  2. extractionextract with EtOAc
  3. dry with materialDry the combined extracts over Na2SO4
  4. concentrationconcentrate

Sources & evidence

ORD record
ord-de92631d282342cab82386bb4ebde842
Source dataset
uspto-grants-2013_10
Patent number
US08552039B2

Reaction notes

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