tert-Butyl Dimethylphosphonoacetate → 6-tert-Butoxycarbonylamino-3-(6-methoxy-pyridin-3-yl)-hex-2-enoic Acid tert-Butyl Ester

HRID 2227260

반응식

HRID 2227260 반응식
COP([CH2:7][C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])(OC)=O.C[Si]([NH-])(C)C.C[Si]([NH-])(C)C.[Na+].[Na+].[C:27]([O:31][C:32](=[O:47])[NH:33][CH2:34][CH2:35][CH2:36][C:37]([C:39]1[CH:40]=[N:41][C:42]([O:45][CH3:46])=[CH:43][CH:44]=1)=O)([CH3:30])([CH3:29])[CH3:28]>O1CCCC1.C(OCC)(=O)C>[C:11]([O:10][C:8](=[O:9])[CH:7]=[C:37]([C:39]1[CH:40]=[N:41][C:42]([O:45][CH3:46])=[CH:43][CH:44]=1)[CH2:36][CH2:35][CH2:34][NH:33][C:32]([O:31][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:47])([CH3:12])([CH3:13])[CH3:14]

참가 물질

6

반응물 3

HCID 4564495tert-Butyl DimethylphosphonoacetateHCID 22086439[4-(6-Methoxy-pyridin-3-yl)-4-oxo-butyl]-carbamic Acid tert-Butyl EsterHCID 86599718Sodiumbis(trimethylsilylamide)

생성물 1

HCID 699879066-tert-Butoxycarbonylamino-3-(6-methoxy-pyridin-3-yl)-hex-2-enoic Acid tert-Butyl Ester

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매2회HCID 8857Ethyl Acetate용매

실험 절차

To a stirred solution of t-butyl dimethylphosphonoacetate (6.86 g, 30.6 mmol) in tetrahydrofuran (150 mL) at −78° C. under argon was added a solution of sodium bis(trimethylsilylamide) (30.6 mL of a 1.0 M solution). After 15 min., a solution of 1-3 (3.0 g, 10.2 mmol) in tetrahydrofuran (30 mL) was added, and the reaction was warmed to ambient temperature, then heated to 40° C. for 1 h. The reaction mixture was then cooled to ambient temperature, diluted with ethyl acetate and washed with saturated aqueous sodium hydrogen carbonate, then saturated aqueous sodium chloride, and dried over anhydrous magnesium sulfate. The reaction mixture was filtered and concentrated at reduced pressure to give an oil that was purified by flash column chromatography (silica gel, 15 to 25% ethyl acetate/hexanes) to give 1-4 and its 2 isomer.

후처리

  1. temperatureheated to 40° C. for 1 h
  2. temperatureThe reaction mixture was then cooled to ambient temperature
  3. washwashed with saturated aqueous sodium hydrogen carbonate
  4. dry with materialsaturated aqueous sodium chloride, and dried over anhydrous magnesium sulfate
  5. filtrationThe reaction mixture was filtered
  6. concentrationconcentrated at reduced pressure
  7. customto give an oil that
  8. customwas purified by flash column chromatography (silica gel, 15 to 25% ethyl acetate/hexanes)
  9. customto give 1-4 and its 2 isomer

출처 및 근거

ORD 기록
ord-37ac060b518c4f7a8b14c5df320cc9c6
출처 데이터셋
uspto-grants-2002_07
특허 번호
US06413955B1

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