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 1160393노트

반응식

HRID 1160393 반응식
[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]

참가 물질

4

반응물 1

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

생성물 1

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

시약·촉매·용매 2

HCID 345198Adams' catalyst촉매HCID 702Ethanol용매2회

실험 절차

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)+.

후처리

  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

출처 및 근거

ORD 기록
ord-5e7d05d288164c9082d295bd102ef399
출처 데이터셋
uspto-grants-2010_10
특허 번호
US07816395B2

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