tert-Butyldimethylsilyl trifluoromethanesulphonate → HCID 86690365, 화합물

HRID 1183145노트

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HRID 1183145 반응식
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[C:10]3[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=13)[N:8]=[CH:7][N:6]([C@H:16]1[CH2:21][CH2:20][O:19][CH2:18][C@@H:17]1[OH:22])[C:5]2=[O:23].[CH3:24][C:25]([Si:28](OS(C(F)(F)F)(=O)=O)([CH3:30])[CH3:29])([CH3:27])[CH3:26].C([O-])(O)=O.[Na+]>C(Cl)Cl.CN(C1C=CN=CC=1)C>[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[C:10]3[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=13)[N:8]=[CH:7][N:6]([C@H:16]1[CH2:21][CH2:20][O:19][CH2:18][C@@H:17]1[O:22][Si:28]([C:25]([CH3:27])([CH3:26])[CH3:24])([CH3:30])[CH3:29])[C:5]2=[O:23]

참가 물질

6

반응물 3

HCID 123564tert-Butyldimethylsilyl trifluoromethanesulphonateHCID 516892Sodium BicarbonateHCID 699279036-bromo-3-[(3R,4S)-3-hydroxytetrahydro-2H-pyran-4-yl]benzo[h]quinazolin-4(3H)-one

생성물 1

HCID 86690365HCID 86690365, 화합물

시약·촉매·용매 2

HCID 142844-(Dimethylamino)pyridine촉매HCID 6344Dichloromethane용매

실험 절차

To a solution of 6-bromo-3-[(3R,4S)-3-hydroxytetrahydro-2H-pyran-4-yl]benzo[h]quinazolin-4(3H)-one (1.00 g, 2.67 mmol) in CH2Cl2 (40 mL) was added DMAP (1.68 g, 13.3 mmol) and then tert-butyl dimethylsilyl trifluoromethane sulfonate (1.84 mL, 8.00 mmol) and the reaction was stirred overnight. The reaction was diluted with saturated, aqueous NaHCO3 and extracted 1× with CH2Cl2. The organics were washed with brine, dried over MgSO4, filtered, concentrated, and dried. The oily residue was purified via silica gel chromatography, eluting with 5-55% ethyl acetate in hexanes to provide 1,5-anhydro-3-(6-bromo-4-oxobenzo quinazolin-3(4H)-yl)-2-O-[tert-butyl(dimethyl)silyl]-3,4-dideoxy-L-threo-pentitol that gave a mass ion (ES+) of 490.8 for [M+H]+.

후처리

  1. extractionextracted 1× with CH2Cl2
  2. washThe organics were washed with brine
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customdried
  7. customThe oily residue was purified via silica gel chromatography
  8. washeluting with 5-55% ethyl acetate in hexanes

출처 및 근거

ORD 기록
ord-3cd387651afd4c289d3c527f4a8d5b6b
출처 데이터셋
uspto-grants-2014_03
특허 번호
US08664234B2

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