Pyridine → (1-Fluorocarbonyl-2-phenyl-propyl)-carbamic acid tert-butyl ester

HRID 1433746

反応式

HRID 1433746 の反応式
[C:1]([O:5][C:6]([NH:8][C@@H:9]([C@H:13]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[CH3:14])[C:10](O)=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].N1C=CC=CC=1.N1C(F)=NC(F)=NC=1[F:29]>ClCCl>[C:1]([O:5][C:6](=[O:7])[NH:8][CH:9]([C:10]([F:29])=[O:11])[CH:13]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[CH3:14])([CH3:4])([CH3:3])[CH3:2]

参加物

5

反応物 3

HCID 1049PyridineHCID 12664Cyanuric fluorideHCID 7021178(2S,3S)-2-((tert-Butoxycarbonyl)amino)-3-phenylbutanoic acid

生成物 1

HCID 87517560(1-Fluorocarbonyl-2-phenyl-propyl)-carbamic acid tert-butyl ester

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

To a solution of (2S,3S)-2-tert-butoxycarbonylamino-3-phenyl-butyric acid (838 mg, 3.0 mmol) in dichloromethane (10 mL) at −35° C. was added dry pyridine (255 μL, 3.15 mmol) and cyanuric fluoride (375 μL, 4.5 mmol) under an atmosphere of dry argon. The mixture was stirred for 1.5 hours while maintaining the temperature between −35 and −25° C. A small amount of ice was added to the reaction mixture and the mixture stirred vigorously for 15 minutes. The organic layer was decanted away from the aqueous solution and the aqueous layer extracted with dichloromethane (2×10 mL). The combined organic layers were washed with ice cold water (15 mL), dried over sodium sulfate, filtered and concentrated in vacuo to give (1-fluorocarbonyl-2-phenyl-propyl)-carbamic acid tert-butyl ester which was used in the subsequent step without further purification.

後処理

  1. temperaturewhile maintaining the temperature between −35 and −25° C
  2. additionA small amount of ice was added to the reaction mixture
  3. stirringthe mixture stirred vigorously for 15 minutes
  4. customThe organic layer was decanted away from the aqueous solution
  5. extractionthe aqueous layer extracted with dichloromethane (2×10 mL)
  6. washThe combined organic layers were washed with ice cold water (15 mL)
  7. dry with materialdried over sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-0dfd7448cbba4e059c35e0105354547d
出典データセット
uspto-grants-2009_11
特許番号
US07612212B2

関連ノート

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