Triphenylphosphine → (S)-Tert-butyl 2-(3'-chlorobiphenyl-4-yl)-1-(1-(2-cyanoethyl)-1H-tetrazol-5-yl)ethylcarbamate

HRID 333336ノート

反応式

HRID 333336 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:23][C:24](=[O:30])[O:25][C:26]([CH3:29])([CH3:28])[CH3:27])[C:16]([NH:18][CH2:19][CH2:20][C:21]#[N:22])=O)=[CH:10][CH:9]=2)[CH:5]=[CH:6][CH:7]=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.CC(OC(/N=N/C(OC(C)C)=O)=O)C.C[Si]([N:68]=[N+:69]=[N-:70])(C)C>C1COCC1>[Cl:1][C:2]1[CH:3]=[C:4]([C:8]2[CH:13]=[CH:12][C:11]([CH2:14][C@H:15]([NH:23][C:24](=[O:30])[O:25][C:26]([CH3:29])([CH3:28])[CH3:27])[C:16]3[N:18]([CH2:19][CH2:20][C:21]#[N:22])[N:70]=[N:69][N:68]=3)=[CH:10][CH:9]=2)[CH:5]=[CH:6][CH:7]=1

参加物

6

反応物 4

HCID 11776TriphenylphosphineHCID 78378AzidotrimethylsilaneHCID 5363146Diisopropyl azodicarboxylateHCID 68748130(S)-Tert-butyl 3-(3'-chlorobiphenyl-4-yl)-1-(2-cyanoethylamino)-1-oxopropan-2-ylcarbamate

生成物 1

HCID 68747779(S)-Tert-butyl 2-(3'-chlorobiphenyl-4-yl)-1-(1-(2-cyanoethyl)-1H-tetrazol-5-yl)ethylcarbamate収率 85%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

To a solution of (S)-tert-butyl 3-(3′-chlorobiphenyl-4-yl)-1-(2-cyanoethylamino)-1-oxopropan-2-ylcarbamate (1.07 g, 2.500 mmol) in THF (50 ml) at room temperature was added Ph3P (1.640 g, 6.25 mmol), and the mixture was stirred at room temperature for 10 minutes. Then, to the mixture at 0° C. was added DIAD (1.215 ml, 6.25 mmol) and 2 minutes later was slowly added trimethylsilyl azide (0.828 ml, 6.25 mmol). The resulting light yellow suspension was slowly warmed up to room temperature and stirred overnight. The reaction mixture was concentrated under reduced pressure. The obtained residue was purified by flash chromatography (silica gel, 25 to 50% EtOAc/Heptane) and gave the title compound: 423 mg (yield: 85%). LCMS (condition B): 453.2 (M+1); retention time=1.23 min.

後処理

  1. temperatureThe resulting light yellow suspension was slowly warmed up to room temperature
  2. stirringstirred overnight
  3. concentrationThe reaction mixture was concentrated under reduced pressure
  4. customThe obtained residue was purified by flash chromatography (silica gel, 25 to 50% EtOAc/Heptane)

出典と根拠

ORDレコード
ord-a6bf42e3a97e41debc9c3e08e4a2cc06
出典データセット
uspto-grants-2014_11
特許番号
US08877815B2

反応ノート

読み込み中…