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

HRID 2227260

反応式

HRID 2227260 の反応式
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]

参加物

6

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒2 回HCID 8857Ethyl Acetate溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-37ac060b518c4f7a8b14c5df320cc9c6
出典データセット
uspto-grants-2002_07
特許番号
US06413955B1

関連ノート

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