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

HRID 246126ノート

反応式

HRID 246126 の反応式
[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]

参加物

8

反応物 4

HCID 1049Pyridine2 回HCID 9845Trifluoroacetic anhydride2 回HCID 10340Sodium CarbonateHCID 22845901((R)-2-carbamoyl-propyl)-carbamic acid tert-butyl ester

生成物 1

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

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒HCID 8857Ethyl Acetate溶媒

実験手順

((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.

後処理

  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)

出典と根拠

ORDレコード
ord-f91ae98f4efb4b41948d326cc2359f3f
出典データセット
uspto-grants-2014_02
特許番号
US08658646B2

反応ノート

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