Triethylamine → HCID 13664796, compound

HRID 2356734Notes

Reaction equation

HRID 2356734 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:9][C:10]([C:17]3[CH:21]=[CH:20][S:19][CH:18]=3)=[C:11](CC(O)=O)[N:12]=2)=[CH:4][CH:3]=1.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=O)C=CC=CC=1.C(N(CC)CC)C>C(O)(C)(C)C>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[O:9][C:10]([C:17]3[CH:21]=[CH:20][S:19][CH:18]=3)=[CH:11][N:12]=2)=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 30697874-Oxazoleacetic acid, 2-(p-fluorophenyl)-5-(3-thienyl)-

Product 1

HCID 13664796HCID 13664796, compoundYield 41.3%

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent

Procedure

A mixture of 2-(4-fluorophenyl)-5-(3-thienyl)oxazol-4-yl acetic acid (1.5 g), diphenylphosphoryl azide (1.28 ml) and triethylamine (0.83 ml) in t-butanol (30 ml) was refluxed for one day. After cooling the reaction mixture, the solvent was removed under reduced pressure. Water was added to the residue and the mixture was extracted with chloroform. The organic layer was washed with a saturated aqueous sodium hydrogen carbonate solution and brine, dried over anhydrous sodium sulfate, and the solvent was removed under reduced pressure. Chloroform was added to the residue, the mixture was heated and insoluble material was removed by filtration, and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (solvent: ethyl acetate:n-hexane=1:9→1:7) to obtain 4-(t-butoxycarbonylamino)methyl-2-(4-fluorophenyl-5-(3-thienyl)oxazole (501 mg).

Workup

  1. temperaturewas refluxed for one day
  2. temperatureAfter cooling the reaction mixture
  3. customthe solvent was removed under reduced pressure
  4. additionWater was added to the residue
  5. extractionthe mixture was extracted with chloroform
  6. washThe organic layer was washed with a saturated aqueous sodium hydrogen carbonate solution and brine
  7. dry with materialdried over anhydrous sodium sulfate
  8. customthe solvent was removed under reduced pressure
  9. additionChloroform was added to the residue
  10. temperaturethe mixture was heated
  11. custominsoluble material was removed by filtration
  12. concentrationthe filtrate was concentrated under reduced pressure
  13. customThe residue was purified by silica gel column chromatography (solvent: ethyl acetate:n-hexane=1:9→1:7)

Sources & evidence

ORD record
ord-faeed8557ac245908cfdfac404cc862b
Source dataset
uspto-grants-2010_07
Patent number
US07759373B2

Reaction notes

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