Pyridine → ((R)-2-cyano-2-methylethyl)-carbamic acid tert-butyl ester

HRID 246126노트

반응식

HRID 246126 반응식
[C:1]([O:5][C:6](=[O:14])[NH:7][CH2:8][C@H:9]([C:11](=O)[NH2:12])[CH3:10])([CH3:4])([CH3:3])[CH3:2].N1C=CC=CC=1.FC(F)(F)C(OC(=O)C(F)(F)F)=O.C(=O)([O-])[O-].[Na+].[Na+]>C1COCC1.C(OCC)(=O)C.O>[C:1]([O:5][C:6](=[O:14])[NH:7][CH2:8][C@H:9]([C:11]#[N:12])[CH3:10])([CH3:2])([CH3:3])[CH3:4]

참가 물질

8

반응물 4

HCID 1049Pyridine2회HCID 9845Trifluoroacetic anhydride2회HCID 10340Sodium CarbonateHCID 22845901((R)-2-carbamoyl-propyl)-carbamic acid tert-butyl ester

생성물 1

HCID 86677951((R)-2-cyano-2-methylethyl)-carbamic acid tert-butyl ester수율 87.9%

시약·촉매·용매 3

HCID 962Water용매HCID 8028Tetrahydrofuran용매HCID 8857Ethyl Acetate용매

실험 절차

((R)-2-Carbamoyl-propyl)-carbamic acid tert-butyl ester (50 mg, 0.247 mmol) was dissolved in THF (1.4 ml). Pyridine (40 ul, 0.49 mmol) and then trifluoroacetic anhydride (42 ul, 0.30 mmol) were added dropwise. The reaction was stirred at room temperature for 1 h and then additional pyridine (40 ul, 0.49 mmol) and trifluoroacetic anhydride (42 ul, 0.30 mmol) were added. The reaction was stirred at room temperature for 16 h then water, sodium carbonate solution and ethyl acetate were added. The aqueous layer was extracted three times with ethyl acetate. The combined organic layers were washed with water and sodium chloride solution, and dried over sodium sulfate. After evaporation, the residue was purified by silica gel chromatography (methanol/dichloromethane) to give 40 mg (87%) of ((R)-2-cyano-2-methyl-ethyl)-carbamic acid tert-butyl ester. (M+Na)+=207.

후처리

  1. stirringThe reaction was stirred at room temperature for 16 h
  2. extractionThe aqueous layer was extracted three times with ethyl acetate
  3. washThe combined organic layers were washed with water and sodium chloride solution
  4. dry with materialdried over sodium sulfate
  5. customAfter evaporation
  6. customthe residue was purified by silica gel chromatography (methanol/dichloromethane)

출처 및 근거

ORD 기록
ord-f91ae98f4efb4b41948d326cc2359f3f
출처 데이터셋
uspto-grants-2014_02
특허 번호
US08658646B2

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