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

HRID 333337Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 333337
[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

Komponenten

4

Edukt 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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  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]

Quellen und Nachweise

ORD-Eintrag
ord-7965d755d5df4660b8f61fcfa507e237
Quelldatensatz
uspto-grants-2014_11
Patentnummer
US08877815B2

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