Citric Acid → benzyl 3-fluoro-4-[(1E)-3-hydroxyprop-1-enyl]phenylcarbamate

HRID 1179489노트

반응식

HRID 1179489 반응식
[H-].C([Al+]CC(C)C)C(C)C.[CH2:11]([O:18][C:19]([NH:21][C:22]1[CH:27]=[CH:26][C:25](/[CH:28]=[CH:29]/[C:30](OC)=[O:31])=[C:24]([F:34])[CH:23]=1)=[O:20])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.C(O)(=O)CC(CC(O)=O)(C(O)=O)O.C(OCC)(=O)C>C1COCC1>[F:34][C:24]1[CH:23]=[C:22]([NH:21][C:19](=[O:20])[O:18][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:27]=[CH:26][C:25]=1/[CH:28]=[CH:29]/[CH2:30][OH:31]

참가 물질

6

반응물 4

HCID 311Citric AcidHCID 8857Ethyl AcetateHCID 21225700Diisobutylaluminumhydride2회HCID 58978082methyl (2E)-3-(4-{[(benzyloxy)carbonyl]amino}-2-fluorophenyl)acrylate

생성물 1

HCID 11392443benzyl 3-fluoro-4-[(1E)-3-hydroxyprop-1-enyl]phenylcarbamate

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

반응 조건

온도
-78 °C

실험 절차

A THF solution of diisobutylaluminum hydride (522 mL of a 1.0 M solution, 522 mmol) was added to a cooled (−78° C.) solution of methyl (2E)-3-(4-{[(benzyloxy)carbonyl]amino}-2-fluorophenyl)acrylate (43 g, 130 mmol) in THF (900 mL). After stirring for one hour at −78° C., additional diisobutylaluminum hydride solution was added (140 mL of a 1.0 M solution, 140 mmol). After another 30 minutes, aqueous citric acid and ethyl acetate were added and the mixture allowed to warm slowly to room temperature. The layers were separated and the aqueous phase extracted with more ethyl acetate. Combined organic phases were washed with H2O, brine and dried (MgSO4), filtered and concentrated to give a red oil. The crude product was purified by column chromatography (0-40% ethyl acetate-hexane) to provide the title compound as a yellow solid.

후처리

  1. waitAfter another 30 minutes
  2. temperatureto warm slowly to room temperature
  3. customThe layers were separated
  4. extractionthe aqueous phase extracted with more ethyl acetate
  5. washCombined organic phases were washed with H2O, brine
  6. dry with materialdried (MgSO4)
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customto give a red oil
  10. customThe crude product was purified by column chromatography (0-40% ethyl acetate-hexane)

출처 및 근거

ORD 기록
ord-d7949f9e021e4314ac64b1f869a1db65
출처 데이터셋
uspto-grants-2007_10
특허 번호
US07279494B2

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