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

HRID 41799Notes

Reaction equation

HRID 41799 reaction equation
C(OC([N:8]([C:34]1[C:43]([N+:44]([O-:46])=[O:45])=[CH:42][CH:41]=[CH:40][C:35]=1[C:36]([O:38][CH3:39])=[O:37])[CH2:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=2[C:22]2[N:26]([CH2:27][C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)[N:25]=[N:24][N:23]=2)=[CH:12][CH:11]=1)=O)(C)(C)C>CO>[CH2:27]([N:26]1[C:22]([C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=2[C:13]2[CH:14]=[CH:15][C:10]([CH2:9][NH:8][C:34]3[C:43]([N+:44]([O-:46])=[O:45])=[CH:42][CH:41]=[CH:40][C:35]=3[C:36]([O:38][CH3:39])=[O:37])=[CH:11][CH:12]=2)=[N:23][N:24]=[N:25]1)[C:28]1[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=1

Participants

3

Reactant 1

HCID 69916454methyl 2-(N-tert-butoxycarbonyl-N-{(2'-[1-benzyl-1H-tetrazol-5-yl]biphenyl-4-yl)methyl}amino)-3-nitrobenzoate2×

Product 1

HCID 69916720methyl 2-[({2'-[1-benzyl-1H-tetrazol-5-yl]biphenyl-4-yl}methyl)amino]-3-nitrobenzoateYield 86.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of methyl 2-(N-tert-butoxycarbonyl-N-{(2′-[1-benzyl-1H-tetrazol-5-yl]biphenyl-4-yl)methyl}amino)-3-nitrobenzoate (compound 20b, 11.93 g, 19.2 mmol) in methanol (15 mL) was added 2NHCl-MeOH (30 mL) under ice-cooling, and the mixture was stirred at the same temperature for 2 hr, and then overnight at room temperature. The reaction mixture was concentrated under reduced pressure, and to the residue were added methanol and diisopropyl ether. The resulting crystals were collected by filtration, washed with diisopropyl ether and hexane, and dried under reduced pressure to give methyl 2-[({2′-[1-benzyl-1H-tetrazol-5-yl]biphenyl-4-yl}methyl)amino]-3-nitrobenzoate (compound 21b) (8.64 g, 86%) as yellow crystals.

Workup

  1. temperaturecooling
  2. customovernight
  3. customat room temperature
  4. concentrationThe reaction mixture was concentrated under reduced pressure
  5. additionto the residue were added methanol and diisopropyl ether
  6. filtrationThe resulting crystals were collected by filtration
  7. washwashed with diisopropyl ether and hexane
  8. customdried under reduced pressure

Sources & evidence

ORD record
ord-f673bebd0bae4cbabfe71de932959902
Source dataset
uspto-grants-2013_09
Patent number
US08530506B2

Reaction notes

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