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Hydrochloric Acid → 2-(4-ethoxy-3-[(2S,3R,4R,5S,6R)-3,4,5-tris(acetyloxy)-6-[(acetyloxy)methyl]tetrahydro-2H-pyran-2-yl]benzyl)azulene-1-carboxylic acid

HRID 1375993
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HRID 1375993 반응식
[OH-].[Na+].[CH2:3]([O:5][C:6]1[CH:26]=[CH:25][C:9]([CH2:10][C:11]2[CH:20]=[C:19]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=[CH:18]3)[C:12]=2[C:21]([O:23]C)=[O:22])=[CH:8][C:7]=1[C@H:27]1[C@H:32]([O:33][C:34](=[O:36])[CH3:35])[C@@H:31]([O:37][C:38](=[O:40])[CH3:39])[C@H:30]([O:41][C:42](=[O:44])[CH3:43])[C@@H:29]([CH2:45][O:46][C:47](=[O:49])[CH3:48])[O:28]1)[CH3:4].Cl>CO>[CH2:3]([O:5][C:6]1[CH:26]=[CH:25][C:9]([CH2:10][C:11]2[CH:20]=[C:19]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=[CH:18]3)[C:12]=2[C:21]([OH:23])=[O:22])=[CH:8][C:7]=1[C@H:27]1[C@@H:32]([O:33][C:34](=[O:36])[CH3:35])[C@@H:31]([O:37][C:38](=[O:40])[CH3:39])[C@@H:30]([O:41][C:42](=[O:44])[CH3:43])[C@@H:29]([CH2:45][O:46][C:47](=[O:49])[CH3:48])[O:28]1)[CH3:4]
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참가 물질

5

반응물 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 58786173methyl 2-(4-ethoxy-3-[(2S,3S,4R,5R,6R)-3,4,5-tris(acetyloxy)-6-[(acetyloxy)methyl]tetrahydro-2H-pyran-2-yl]benzyl)azulene-1-carboxylate

생성물 1

HCID 693824782-(4-ethoxy-3-[(2S,3R,4R,5S,6R)-3,4,5-tris(acetyloxy)-6-[(acetyloxy)methyl]tetrahydro-2H-pyran-2-yl]benzyl)azulene-1-carboxylic acid수율 70.5%

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

10% aqueous solution of sodiumhydroxide (5.0 ml) was added dropwise to a solution of methyl 2-(4-ethoxy-3-[(2S,3S,4R,5R,6R)-3,4,5-tris(acetyloxy)-6-[(acetyloxy) methyl]tetrahydro-2H-pyran-2-yl]benzyl)azulene-1-carboxylate (0.58 g) in methanol (5.0 ml) at room temperature. The mixture was stirred for 30 minutes and refluxed with heating for further six hours. After cooling with ice, the reaction mixture was neutralized by adding 10% aqueous solution of hydrochloric acid. The neutralized product was extracted with chloroform. The organic layer was washed with saturated brine and dried over anhydrous sodium sulfate. After filtration, the filtrate was concentrated. The residue was purified by silica gel column chromatography (chloroform-methanol) to obtain 2-(4-ethoxy-3-[(2S,3R,4R,5S,6R)-3,4,5-tris(acetyloxy)-6-[(acetyloxy)methyl]tetrahydro-2H-pyran-2-yl]benzyl)azulene-1-carboxylic acid (0.4 g).

후처리

  1. temperaturerefluxed
  2. temperaturewith heating for further six hours
  3. temperatureAfter cooling with ice
  4. extractionThe neutralized product was extracted with chloroform
  5. washThe organic layer was washed with saturated brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. filtrationAfter filtration
  8. concentrationthe filtrate was concentrated
  9. customThe residue was purified by silica gel column chromatography (chloroform-methanol)

출처 및 근거

ORD 기록
ord-3b96519c882a47f1acbc8574c92c8c0c
출처 데이터셋
uspto-grants-2007_01
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07169761B2

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