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Triethylamine → HCID 13664796, 화합물

HRID 2356734
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HRID 2356734 반응식
[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
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 3

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

생성물 1

HCID 13664796HCID 13664796, 화합물수율 41.3%

시약·촉매·용매 1

HCID 6386tert-Butanol용매

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-faeed8557ac245908cfdfac404cc862b
출처 데이터셋
uspto-grants-2010_07
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07759373B2

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