1,8-Diazabicyclo(5.4.0)undec-7-ene → (S)-Tert-butyl 2-(3'-chlorobiphenyl-4-yl)-1-(1H-tetrazol-5-yl)ethylcarbamate

HRID 333337ノート

反応式

HRID 333337 の反応式
[Cl:1][C:2]1[CH:3]=[C:4]([C:8]2[CH:13]=[CH:12][C:11]([CH2:14][C@H:15]([NH:25][C:26](=[O:32])[O:27][C:28]([CH3:31])([CH3:30])[CH3:29])[C:16]3[N:20](CCC#N)[N:19]=[N:18][N:17]=3)=[CH:10][CH:9]=2)[CH:5]=[CH:6][CH:7]=1.C1CCN2C(=NCCC2)CC1>C(Cl)Cl>[Cl:1][C:2]1[CH:3]=[C:4]([C:8]2[CH:9]=[CH:10][C:11]([CH2:14][C@H:15]([NH:25][C:26](=[O:32])[O:27][C:28]([CH3:30])([CH3:29])[CH3:31])[C:16]3[NH:20][N:19]=[N:18][N:17]=3)=[CH:12][CH:13]=2)[CH:5]=[CH:6][CH:7]=1

参加物

4

反応物 2

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 68747779(S)-Tert-butyl 2-(3'-chlorobiphenyl-4-yl)-1-(1-(2-cyanoethyl)-1H-tetrazol-5-yl)ethylcarbamate

生成物 1

HCID 178454141(S)-Tert-butyl 2-(3'-chlorobiphenyl-4-yl)-1-(1H-tetrazol-5-yl)ethylcarbamate収率 94%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

To a suspension of (S)-tert-butyl 2-(3′-chlorobiphenyl-4-yl)-1-(1-(2-cyanoethyl)-1H-tetrazol-5-yl)ethylcarbamate (300 mg, 0.662 mmol) in DCM (3 ml) at room temperature was added DBU (2 ml, 13.27 mmol), and the solution was stirred at room temperature for 1.5 hours. The reaction mixture was concentrated reduced pressure. The obtained residue was purified by reverse phase HPLC [30 to 95% ACN-water (0.1% TFA) over 10 min by Sunfire C18 column] and gave the title compound: 250 mg (yield: 94%). LCMS (condition F): 400.1 (M+1); retention time=1.28 min.

後処理

  1. concentrationThe reaction mixture was concentrated reduced pressure
  2. customThe obtained residue was purified by reverse phase HPLC [30 to 95% ACN-water (0.1% TFA) over 10 min by Sunfire C18 column]

出典と根拠

ORDレコード
ord-7965d755d5df4660b8f61fcfa507e237
出典データセット
uspto-grants-2014_11
特許番号
US08877815B2

反応ノート

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