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

HRID 1616641Notes

Reaction equation

HRID 1616641 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-754cf584ad4c4c8e9385fff9a6b02e0b
Source dataset
uspto-grants-2014_07
Patent number
US08765796B2

Reaction notes

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