1,1-Dimethylethyl (3S)-4-azido-3-[(3-chloro-4-cyanophenyl)amino]butanoate → 1,1-Dimethylethyl (3S)-4-amino-3-[(3-chloro-4-cyanophenyl)amino]butanoate

HRID 1160393ノート

反応式

HRID 1160393 の反応式
[N:1]([CH2:4][C@@H:5]([NH:14][C:15]1[CH:20]=[CH:19][C:18]([C:21]#[N:22])=[C:17]([Cl:23])[CH:16]=1)[CH2:6][C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])=[N+]=[N-]>CCO.O=[Pt]=O>[NH2:1][CH2:4][C@@H:5]([NH:14][C:15]1[CH:20]=[CH:19][C:18]([C:21]#[N:22])=[C:17]([Cl:23])[CH:16]=1)[CH2:6][C:7]([O:9][C:10]([CH3:11])([CH3:13])[CH3:12])=[O:8]

参加物

4

反応物 1

HCID 866183611,1-Dimethylethyl (3S)-4-azido-3-[(3-chloro-4-cyanophenyl)amino]butanoate

生成物 1

HCID 595161531,1-Dimethylethyl (3S)-4-amino-3-[(3-chloro-4-cyanophenyl)amino]butanoate収率 84.1%

試薬・触媒・溶媒 2

HCID 345198Adams' catalyst触媒HCID 702Ethanol溶媒2 回

実験手順

PtO2 (0.98 g) in EtOH (100 mL) was reduced with H2 (40 psi) on a Parr shaker for 20 minutes. To this mixture was added a solution of 1,1-dimethylethyl (3S)-4-azido-3-[(3-chloro-4-cyanophenyl)amino]butanoate (25.5 g, 76 mmol) in EtOH (100 mL) and the reaction was shaken on a Parr shaker under H2 (35 psi) for 2.5 h. The reaction mixture was filtered through a pad Celite and concentrated. The residue was dissolved in CH2Cl2, washed with H2O, dried over MgSO4, filtered and the solvent removed. The residue was triturated with Et2O (75 mL), chilled, and filtered to afford the titled product (19.8 g, 84%). 1H-NMR (CD3OD) δ: 1.39 (9H, s), 2.39 (1H, m), 2.58 (1H, m), 2.73 (1H, m), 2.79 (1H, m), 3.97 (1H, m), 6.68 (1H, d, J=8 Hz), 6.84 (1H, s), 7.44 (1H, d, J=8.8 Hz). LC-MS (ES) m/e 310.6 (M+H)+.

後処理

  1. filtrationThe reaction mixture was filtered through a pad Celite
  2. concentrationconcentrated
  3. dissolutionThe residue was dissolved in CH2Cl2
  4. washwashed with H2O
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. customthe solvent removed
  8. customThe residue was triturated with Et2O (75 mL)
  9. temperaturechilled
  10. filtrationfiltered

出典と根拠

ORDレコード
ord-5e7d05d288164c9082d295bd102ef399
出典データセット
uspto-grants-2010_10
特許番号
US07816395B2

反応ノート

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