Water → [(S)-2-(3'-methyl-biphenyl-4-yl)-1-(1H-tetrazol-5-yl)-ethyl]-carbamic acid tert-butyl ester

HRID 333341Notes

Reaction equation

HRID 333341 reaction equation
[C:1]([C@@H:3]([NH:18][C:19](=[O:25])[O:20][C:21]([CH3:24])([CH3:23])[CH3:22])[CH2:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([CH3:17])[CH:12]=2)=[CH:7][CH:6]=1)#[N:2].[N-:26]=[N+:27]=[N-:28].[Na+].O>C(O)(C)C.CCOC(C)=O.[Br-].[Zn+2].[Br-]>[C:21]([O:20][C:19](=[O:25])[NH:18][C@H:3]([C:1]1[NH:28][N:27]=[N:26][N:2]=1)[CH2:4][C:5]1[CH:6]=[CH:7][C:8]([C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([CH3:17])[CH:12]=2)=[CH:9][CH:10]=1)([CH3:22])([CH3:24])[CH3:23]

Participants

7

Reactant 3

HCID 962WaterHCID 33557Sodium AzideHCID 68750114(S)-tert-butyl 1-cyano-2-(3'-methylbiphenyl-4-yl)ethylcarbamate

Product 1

HCID 178424510[(S)-2-(3'-methyl-biphenyl-4-yl)-1-(1H-tetrazol-5-yl)-ethyl]-carbamic acid tert-butyl ester

Reagents, catalysts & solvents 3

HCID 10421208Zinc bromideCatalystHCID 3776IsopropanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

(S)-tert-butyl 1-cyano-2-(3′-methylbiphenyl-4-yl)ethylcarbamate (0.81 g, 2.408 mmol), sodium azide (0.344 g, 5.30 mmol) and zinc bromide (0.325 g, 1.445 mmol) were refluxed in i-propanol (15 mL) and H2O (30 mL) for 6 hours. The reaction mixture was cooled to room temperature, diluted with EtOAc, and washed with 1M HCl and brine. The organic layer was dried over Na2SO4 and concentrated under reduced pressure. The obtained residue was purified by silica gel flash column chromatography (EtOAc/heptane->10% MeOH in DCM/DCM) to give [(S)-2-(3′-methyl-biphenyl-4-yl)-1-(1H-tetrazol-5-yl)-ethyl]-carbamic acid tert-butyl ester. 1H NMR (400 MHz, DMSO-d6) δ 1.30 (s, 9H), 2.36 (s, 3H), 3.10-3.21 (m, 1H), 3.24-3.31 (m, 1H), 4.96-5.15 (m, 1H), 7.15 (d, J=7.33 Hz, 1H), 7.27-7.35 (m, 3H), 7.39-7.46 (m, 2H), 7.55 (d, J=8.08 Hz, 2H), 7.65 (d, J=8.34 Hz, 1H); MS: m/z (MH+) 380; Retention time=1.51 min. (condition A)

Workup

  1. washwashed with 1M HCl and brine
  2. dry with materialThe organic layer was dried over Na2SO4
  3. concentrationconcentrated under reduced pressure
  4. customThe obtained residue was purified by silica gel flash column chromatography (EtOAc/heptane->10% MeOH in DCM/DCM)

Sources & evidence

ORD record
ord-a6cda00bcec4418eb08b4d0ca9ebe1b0
Source dataset
uspto-grants-2014_11
Patent number
US08877815B2

Reaction notes

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