Potassium Carbonate → methyl 2-(N-tert-butoxycarbonyl-N-{(2'-[1-benzyl-1H-tetrazol-5-yl]biphenyl-4-yl)methyl}amino)-3-nitrobenzoate

HRID 41798Notes

Reaction equation

HRID 41798 reaction equation
[CH2:1]([N:8]1[C:12]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[C:19]2[CH:24]=[CH:23][C:22]([CH2:25]Br)=[CH:21][CH:20]=2)=[N:11][N:10]=[N:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:27]([O:31][C:32]([NH:34][C:35]1[C:44]([N+:45]([O-:47])=[O:46])=[CH:43][CH:42]=[CH:41][C:36]=1[C:37]([O:39][CH3:40])=[O:38])=[O:33])([CH3:30])([CH3:29])[CH3:28].C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[C:27]([O:31][C:32]([N:34]([C:35]1[C:44]([N+:45]([O-:47])=[O:46])=[CH:43][CH:42]=[CH:41][C:36]=1[C:37]([O:39][CH3:40])=[O:38])[CH2:25][C:22]1[CH:23]=[CH:24][C:19]([C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=2[C:12]2[N:8]([CH2:1][C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)[N:9]=[N:10][N:11]=2)=[CH:20][CH:21]=1)=[O:33])([CH3:30])([CH3:28])[CH3:29]

Participants

5

Reactant 3

HCID 11430Potassium Carbonate2×HCID 9965968Methyl 2-((tert-butoxycarbonyl)amino)-3-nitrobenzoate2×HCID 230199841-benzyl-5-[4'-(bromomethyl)biphenyl-2-yl]-1H-tetrazole2×

Product 1

HCID 69916454methyl 2-(N-tert-butoxycarbonyl-N-{(2'-[1-benzyl-1H-tetrazol-5-yl]biphenyl-4-yl)methyl}amino)-3-nitrobenzoateYield 81.7%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 1-benzyl-5-[4′-(bromomethyl)biphenyl-2-yl]-1H-tetrazole (compound 5b, 9.82 g, 24 mmol), methyl 2-(tert-butoxycarbonylamino)-3-nitrobenzoate (compound 19a, 7.32 g, 24.7 mmol) and potassium carbonate (3.68 g, 26.7 mmol) in acetonitrile (100 mL) was heated under reflux for 6 hr under argon stream. To the reaction mixture was added potassium carbonate (1.34 g), and the mixture was heated under reflux for 3 hr. The reaction mixture was cooled and filtered. The insoluble material was washed with chloroform. The filtrate and washing were combined, and concentrated under reduced pressure. The concentrated residue was purified by silica gel column (hexane→hexane:AcOEt=5:1→4:1→3:1→2:1→3:2) to give methyl 2-(N-tert-butoxycarbonyl-N-{(2′-[1-benzyl-1H-tetrazol-5-yl]biphenyl-4-yl)methyl}amino)-3-nitrobenzoate (compound 20b) (12.17 g, 81%) as a yellow amorphous solid.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 6 hr under argon stream
  3. temperaturethe mixture was heated
  4. temperatureunder reflux for 3 hr
  5. temperatureThe reaction mixture was cooled
  6. filtrationfiltered
  7. washThe insoluble material was washed with chloroform
  8. washThe filtrate and washing
  9. concentrationconcentrated under reduced pressure
  10. customThe concentrated residue was purified by silica gel column (hexane→hexane:AcOEt=5:1→4:1→3:1→2:1→3:2)

Sources & evidence

ORD record
ord-ea001cdfd61b41a89a6f9365c9c092aa
Source dataset
uspto-grants-2013_09
Patent number
US08530506B2

Reaction notes

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