Pivaloyl chloride → 1-(1-Naphthalen-1-yl-ethyl)-aziridine-2-carboxylic acid but-3-enyl-phenethyl-amide

HRID 222488

反応式

HRID 222488 の反応式
CO[C:3]([CH:5]1[CH2:7][N:6]1[CH:8]([C:10]1[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[CH:13]=[CH:12][CH:11]=1)[CH3:9])=[O:4].O([Si](C)(C)C)[K].CC(C)(C)C(Cl)=O.[CH2:33]([NH:37][CH2:38][CH2:39][C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1)[CH2:34][CH:35]=[CH2:36].C(=O)(O)[O-].[Na+]>C1COCC1>[CH2:33]([N:37]([CH2:38][CH2:39][C:40]1[CH:41]=[CH:42][CH:43]=[CH:44][CH:45]=1)[C:3]([CH:5]1[CH2:7][N:6]1[CH:8]([C:10]1[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[CH:13]=[CH:12][CH:11]=1)[CH3:9])=[O:4])[CH2:34][CH:35]=[CH2:36]

参加物

7

反応物 5

HCID 62493Pivaloyl chlorideHCID 516892Sodium BicarbonateHCID 16720109N-(2-phenylethyl)but-3-en-1-amineHCID 866010811-(1-Naphthalen-1-yl-ethyl)-aziridine-2-carboxylic acid methyl esterHCID 178504318HCID 178504318、化合物

生成物 1

HCID 866010821-(1-Naphthalen-1-yl-ethyl)-aziridine-2-carboxylic acid but-3-enyl-phenethyl-amide収率 76.4%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

To a solution of 1 (12.6 g, 49.75 mmol) in THF (200 mL) is added KOTMS (6.38 g, 49.75 mmol). The mixture is stirred overnight at room temperature. The mixture is concentrated and the residue dissolved in dichloromethane (200 mL) and cooled to 0° C. Trimethylacetyl chloride (5.94 g, 49.25 mmol) is added slowly and the mixture is warmed to room temperature over 2 hours. The mixture is cooled to −78° C., 2 (8.63 g, 49.25 mmol) is added and stirring continued at −78° C. for 1.5 h. Saturated sodium bicarbonate (100 mL) is added and the mixture is allowed to warm to rt. The mixture is extracted with EtOAc (4×100 mL) and the organic extracts are combined, dried and concentrated under vacuum. The residue is purified by flash chromatography (silica gel; Hexane/EtOAc 1:8) to provide 15 g (76%) of the title compound as a mixture of two diastereomers in an equimolecular ratio. M+H+=399.37.

後処理

  1. concentrationThe mixture is concentrated
  2. dissolutionthe residue dissolved in dichloromethane (200 mL)
  3. temperaturecooled to 0° C
  4. temperaturethe mixture is warmed to room temperature over 2 hours
  5. temperatureThe mixture is cooled to −78° C.
  6. stirringstirring
  7. waitcontinued at −78° C. for 1.5 h
  8. temperatureto warm to rt
  9. extractionThe mixture is extracted with EtOAc (4×100 mL)
  10. customdried
  11. concentrationconcentrated under vacuum
  12. customThe residue is purified by flash chromatography (silica gel; Hexane/EtOAc 1:8)

出典と根拠

ORDレコード
ord-69cf5403e4eb400ca81dd051f336b710
出典データセット
uspto-grants-2012_06
特許番号
US08207183B2

関連ノート

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