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

HRID 1179489ノート

反応式

HRID 1179489 の反応式
[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]

参加物

6

反応物 4

HCID 311Citric AcidHCID 8857Ethyl AcetateHCID 21225700Diisobutylaluminumhydride2 回HCID 58978082methyl (2E)-3-(4-{[(benzyloxy)carbonyl]amino}-2-fluorophenyl)acrylate

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
-78 °C

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-d7949f9e021e4314ac64b1f869a1db65
出典データセット
uspto-grants-2007_10
特許番号
US07279494B2

反応ノート

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