Hydrochloric Acid → HCID 178440077, compound

HRID 52986

Reaction equation

HRID 52986 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1[CH:14]=[CH:13][C:12]([CH2:15][N:16]2[C:20]([C:21]([O:23][CH2:24][CH3:25])=[O:22])=[C:19]([C:26]([OH:29])([CH3:28])[CH3:27])[N:18]=[C:17]2[CH2:30][CH2:31][CH3:32])=[CH:11][CH:10]=1)#[N:2].C([Sn]([N:46]=[N+:47]=[N-:48])(CCCC)CCCC)CCC.C(=O)([O-])O.[Na+].Cl>C1(C)C=CC=CC=1.C(OCC)(=O)C.O>[OH:29][C:26]([C:19]1[N:18]=[C:17]([CH2:30][CH2:31][CH3:32])[N:16]([CH2:15][C:12]2[CH:13]=[CH:14][C:9]([C:4]3[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=3[C:1]3[NH:48][N:47]=[N:46][N:2]=3)=[CH:10][CH:11]=2)[C:20]=1[C:21]([O:23][CH2:24][CH3:25])=[O:22])([CH3:27])[CH3:28]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 4984872Tributyltin azideHCID 15461993Ethyl 1-((2'-cyano(1,1'-biphenyl)-4-yl)methyl)-4-(1-hydroxy-1-methylethyl)-2-propyl-1H-imidazole-5-carboxylate

Product 1

HCID 178440077HCID 178440077, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 1.00 g of ethyl 1-(2'-cyanobiphenyl-4-yl)methyl-4-(1-hydroxy-1-methylethyl)-2-propylimidazole-5-carboxylate [prepared as described in Example 71(b)] and 100 g of tributyltin azide in 7.5 ml of toluene was stirred at 100° C. for 5 days. 2.5 g of sodium hydrogencarbonate and 20 ml of water were then added to the mixture, and the resulting mixture was stirred at room temperature for 8 hours. At the end of this time, the mixture was diluted with ethyl acetate and acidified with 3N aqueous hydrochloric acid to a pH value of 3. The ethyl acetate layer was separated, dried over anhydrous magnesium sulfate and concentrated by evaporation under reduced pressure, to give ethyl 4-(1-hydroxy-1-methylethyl)-2-propyl-1-{4-[2-(tetrazol-5-yl)phenyl]phenyl}methylimidazole-5-carboxylate as a syrup. 0.80 g of trityl chloride was added to a solution of the whole of this syrup in 15 ml of pyridine, and the mixture was stirred at 60° C. for 4 hours. At the end of this time, the reaction mixture was concentrated by evaporation under reduced pressure, and the residue was purified by column chromatography through silica gel, using a 1:1 by volume mixture of ethyl acetate and hexane as the eluent; it was then crystallized in diisopropyl ether, to give 1.15 g of the title compound as crystals.

Workup

  1. customThe ethyl acetate layer was separated
  2. dry with materialdried over anhydrous magnesium sulfate
  3. concentrationconcentrated by evaporation under reduced pressure

Sources & evidence

ORD record
ord-632fcdb4843d4784b5b8a7569b5ca0ed
Source dataset
uspto-grants-1997_04
Patent number
US05616599

Linked notes

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