1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → (S)-tert-butyl 2-(methylamino)-2-oxo-1-phenylethylcarbamate

HRID 456349ノート

反応式

HRID 456349 の反応式
[C:1]([O:5][C:6]([NH:8][C@@H:9]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[C:10](O)=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].Cl.CN.C1C=CC2N(O)N=[N:28][C:26]=2C=1.CCN(C(C)C)C(C)C.CCN=C=NCCCN(C)C>CN(C=O)C.C(Cl)Cl>[CH3:26][NH:28][C:10](=[O:11])[C@@H:9]([NH:8][C:6](=[O:7])[O:5][C:1]([CH3:4])([CH3:3])[CH3:2])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

参加物

8

反応物 5

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 6364545Methylamine hydrochlorideHCID 11010409(2S)-2-(((tert-butoxy)carbonyl)amino)-2-phenylacetic acid

生成物 1

HCID 59979465(S)-tert-butyl 2-(methylamino)-2-oxo-1-phenylethylcarbamate収率 99%

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 6344Dichloromethane溶媒

反応条件

温度
0 °C

実験手順

To a solution of (S)-2-(tert-butoxycarbonylamino)-2-phenylacetic acid (1.00 g, 3.98 mmol) in DMF (5 mL) and methylene chloride (5 mL) was added methylamine hydrochloride (403 mg, 5.97 mmol), HOBt (645 mg, 4.78 mmol), and Hunig's Base (1.73 mL, 9.95 mmol) and the resulting solution stirred at 0° C. for 10 minutes. EDCI (916 mg, 4.78 mmol) was added and the reaction stirred at 25° C. for 18 hours. The mixture was concentrated in vacuo, the resulting residue was diluted with ethyl acetate (45 mL), brine (10 mL), and 5% H3PO4 aqueous solution (10 mL), and the layers were separated. The organic layer was washed with 5% H3PO4 aqueous solution (10 mL), twice with saturated aqueous sodium bicarbonate solution (15 mL), water (15 mL), and brine (15 mL). The organic layer was dried over sodium sulfate, filtered, and concentrated in vacuo to afford the title compound as a light colored solid. The crude material was taken on directly to the next step. (1.04 g, 99% yield) MS (ESI+) m/z=265 (M+H)+.

後処理

  1. stirringthe reaction stirred at 25° C. for 18 hours
  2. concentrationThe mixture was concentrated in vacuo
  3. additionthe resulting residue was diluted with ethyl acetate (45 mL), brine (10 mL), and 5% H3PO4 aqueous solution (10 mL)
  4. customthe layers were separated
  5. washThe organic layer was washed with 5% H3PO4 aqueous solution (10 mL), twice with saturated aqueous sodium bicarbonate solution (15 mL), water (15 mL), and brine (15 mL)
  6. dry with materialThe organic layer was dried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-8c1ecbd6a80248c7a36989a1749bc4b4
出典データセット
uspto-grants-2013_07
特許番号
US08497275B2

反応ノート

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