Acetic Anhydride → HCID 86703444, 화합물

HRID 245597노트

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HRID 245597 반응식
[Si:1]([O:8][C@H:9]1[C@H:22](/[CH:23]=[CH:24]/[C@@H:25]([O:31][Si:32]([C:35]([CH3:38])([CH3:37])[CH3:36])([CH3:34])[CH3:33])[CH2:26][CH2:27][CH2:28][CH2:29][CH3:30])[C@H:12]2[CH2:13][C:14]3[CH:15]=[CH:16][CH:17]=[C:18]([OH:21])[C:19]=3[CH2:20][C@H:11]2[CH2:10]1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[C:39](OC(=O)C)(=[O:41])[CH3:40]>C1(C)C=CC=CC=1.CN(C1C=CN=CC=1)C.C(=O)(O)[O-].[Na+]>[C:39]([O:21][C:18]1[CH:17]=[CH:16][CH:15]=[C:14]2[C:19]=1[CH2:20][C@H:11]1[CH2:10][C@@H:9]([O:8][Si:1]([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2])[C@H:22](/[CH:23]=[CH:24]/[C@@H:25]([O:31][Si:32]([C:35]([CH3:37])([CH3:36])[CH3:38])([CH3:34])[CH3:33])[CH2:26][CH2:27][CH2:28][CH2:29][CH3:30])[C@H:12]1[CH2:13]2)(=[O:41])[CH3:40]

참가 물질

6

반응물 2

HCID 7918Acetic AnhydrideHCID 86677387HCID 86677387, 화합물

생성물 1

HCID 86703444HCID 86703444, 화합물수율 84.1%

시약·촉매·용매 3

HCID 142844-(Dimethylamino)pyridine촉매HCID 1140Toluene용매HCID 516892Sodium Bicarbonate용매

실험 절차

(1R,2R,3aS,9aS)-2,3,3a,4,9,9a-hexahydro-2-(tert-butyldimethylsilyoxy)-1-((S,E)-3-(tert-butyldimethylsilyoxy)oct-1-enyl)-1H-cyclopenta[b]naphthalen-5-ol (0.5 g, 0.89 mmol) in toluene (5 ml) was treated with acetic anhydride (0.1 ml, 1.07 mmol) and DMAP (1.1 mg, 0.09 mmol) at room temperature for 30 minutes. The reaction was diluted with saturated sodium bicarbonate aqueous (10 ml) and extracted with ethyl acetate (10 ml). The reaction mixture was phase separated and the aqueous layer was extracted with ethyl acetate. The organic layers were combined and dried over anhydrous magnesium sulfate. The solid was filtered off. The solvent was evaporated off under vacuum. The crude product was purified by chromatography on silica gel using a mixture of hexane and ethyl acetate as a gradient eluent. 0.45 g (1R,2R,3aS,9aS)-2,3,3a,4,9,9a-hexahydro-2-(tert-butyldimethylsilyoxy)-1-((S,E)-3-(tert-butyldimethylsilyoxy)oct-1-enyl)-1H-cyclopenta[b]naphthalen-5-yl acetate was obtained. The product was then dissolved in tetrahydrofuran (0.9 ml), and treated with acetic acid (2.7 ml) and distilled water (0.9 ml) overnight at room temperature. The reaction was then diluted with saturated sodium bicarbonate aqueous (12 ml) and extracted with ethyl acetate (15 ml). The reaction mixture was phase separated and the aqueous layer was extracted with ethyl acetate. The organic layers were combined and dried over anhydrous magnesium sulfate. The solid was filtered off. The solvent was evaporated off under vacuum. The crude product was purified by chromatography on silica gel using a mixture of hexane and ethyl acetate as a gradient eluent. The titled compound was obtained in a crystalline form. Melting range was 54˜65° C. Yield: 65%.

후처리

  1. extractionextracted with ethyl acetate (10 ml)
  2. customseparated
  3. extractionthe aqueous layer was extracted with ethyl acetate
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationThe solid was filtered off
  6. customThe solvent was evaporated off under vacuum
  7. customThe crude product was purified by chromatography on silica gel using
  8. additiona mixture of hexane and ethyl acetate as a gradient eluent

출처 및 근거

ORD 기록
ord-57d5be37235448198c12ccdc41fc011e
출처 데이터셋
uspto-grants-2014_02
특허 번호
US08658837B2

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