Potassium Carbonate → Ethyl 4-(2-hydroxypropan-2-yl)-2-propyl-1-((2'-(1-trityl-1H-tetrazol-5-yl)biphenyl-4-yl)methyl)-1H-imidazole-5-carboxylate

HRID 554018Notes

Reaction equation

HRID 554018 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[NH:10][C:9]([CH2:11][CH2:12][CH3:13])=[N:8][C:7]=1[C:14]([OH:17])([CH3:16])[CH3:15])=[O:5])[CH3:2].[C:18]1([C:24]([C:50]2[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=2)([C:44]2[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=2)[N:25]2[C:29]([C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=3[C:36]3[CH:41]=[CH:40][C:39]([CH2:42]Br)=[CH:38][CH:37]=3)=[N:28][N:27]=[N:26]2)[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.C(=O)([O-])[O-].[K+].[K+]>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.CC(C)=O>[CH2:1]([O:3][C:4]([C:6]1[N:10]([CH2:42][C:39]2[CH:38]=[CH:37][C:36]([C:31]3[CH:32]=[CH:33][CH:34]=[CH:35][C:30]=3[C:29]3[N:25]([C:24]([C:50]4[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=4)([C:44]4[CH:45]=[CH:46][CH:47]=[CH:48][CH:49]=4)[C:18]4[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=4)[N:26]=[N:27][N:28]=3)=[CH:41][CH:40]=2)[C:9]([CH2:11][CH2:12][CH3:13])=[N:8][C:7]=1[C:14]([OH:17])([CH3:15])[CH3:16])=[O:5])[CH3:2]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 100534615-(4'-(Bromomethyl)(1,1'-biphenyl)-2-yl)-1-trityl-1H-tetraazoleHCID 178440079HCID 178440079, compound

Product 1

HCID 19036118Ethyl 4-(2-hydroxypropan-2-yl)-2-propyl-1-((2'-(1-trityl-1H-tetrazol-5-yl)biphenyl-4-yl)methyl)-1H-imidazole-5-carboxylateYield 93.9%

Reagents, catalysts & solvents 2

HCID 74236Tetrabutylammonium BromideCatalystHCID 180AcetoneSolvent

Procedure

4-(1-Hydroxy-1-methylethyl)-2-propyl-1H-imidazole-5-carboxylic acid ethyl ester (100 g), N-(triphenylmethyl)-5-(4′-bromomethyl biphenyl-2-yl)tetrazole (250 g), potassium carbonate (170 g) & tetra butyl ammonium bromide (15 g) in acetone (2.5 L) were refluxed for 10-16 hours. Progress of reaction was monitor by HPLC. After completion of reaction, reaction mass was cooled and filtered to remove the salts. Inorganic salts were washed with acetone (300 mL). Acetone from combine the filtrate and washings was distilled. The residue obtained was crystallized in acetonitrile to get ethyl-4-(1-hydroxy-1-methylethyl)-2-propyl-1-{4-[2-(trityltetrazol-5-yl)phenyl]phenyl}methylimidazole-5-carboxylate (280 g).

Workup

  1. customProgress of reaction
  2. customAfter completion of reaction, reaction mass
  3. temperaturewas cooled
  4. filtrationfiltered
  5. customto remove the salts
  6. washInorganic salts were washed with acetone (300 mL)
  7. distillationAcetone from combine the filtrate and washings was distilled
  8. customThe residue obtained
  9. customwas crystallized in acetonitrile

Sources & evidence

ORD record
ord-081ca7045a0d4afd80deea51f0b87b9d
Source dataset
uspto-grants-2011_11
Patent number
US08048904B2

Reaction notes

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