Hydrochloric Acid → Methyl 2-butyl-1-[(2'-carboxybiphenyl-4-yl)methyl]-4-(methoxymethyl)imidazole-5-carboxylate

HRID 52883Notes

Reaction equation

HRID 52883 reaction equation
C([O:5][C:6]([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[C:14]1[CH:19]=[CH:18][C:17]([CH2:20][N:21]2[C:25]([C:26]([O:28][CH3:29])=[O:27])=[C:24]([CH2:30][O:31][CH3:32])[N:23]=[C:22]2[CH2:33][CH2:34][CH2:35][CH3:36])=[CH:16][CH:15]=1)=[O:7])(C)(C)C.Cl>O1CCOCC1>[CH2:33]([C:22]1[N:21]([CH2:20][C:17]2[CH:16]=[CH:15][C:14]([C:9]3[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=3[C:6]([OH:7])=[O:5])=[CH:19][CH:18]=2)[C:25]([C:26]([O:28][CH3:29])=[O:27])=[C:24]([CH2:30][O:31][CH3:32])[N:23]=1)[CH2:34][CH2:35][CH3:36]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 19036253Methyl 1-[(2'-t-butoxycarbonylbiphenyl-4-yl)methyl]-2-butyl-4-(methoxymethyl)imidazole-5-carboxylate

Product 1

HCID 19036151Methyl 2-butyl-1-[(2'-carboxybiphenyl-4-yl)methyl]-4-(methoxymethyl)imidazole-5-carboxylateYield 97.8%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A solution of 0.30 g of methyl 1-[(2'-t-butoxycarbonylbiphenyl-4-yl)methyl]-2-butyl-4-(methoxymethyl)imidazole-5-carboxylate (prepared as described in Example 8) in 3 ml of a 4N solution of hydrogen chloride in dioxane was allowed no stand at room temperature for 5 hours, after which the solvent was removed by distillation under reduced pressure. The syrupy residue was triturated in diethyl ether and collected by filtration, to give 0.26 g of the title compound in the form of its hydrochloride, melting at 106°-110° C. (with softening).

Workup

  1. customat room temperature
  2. customfor 5 hours
  3. customafter which the solvent was removed by distillation under reduced pressure
  4. customThe syrupy residue was triturated in diethyl ether
  5. filtrationcollected by filtration

Sources & evidence

ORD record
ord-3c3265b24db644e8a6eb50a4a367af8a
Source dataset
uspto-grants-1997_04
Patent number
US05616599

Reaction notes

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