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

HRID 333337Notes

Reaction equation

HRID 333337 reaction equation
[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

Participants

4

Reactant 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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

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.

Workup

  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]

Sources & evidence

ORD record
ord-7965d755d5df4660b8f61fcfa507e237
Source dataset
uspto-grants-2014_11
Patent number
US08877815B2

Reaction notes

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