Hydrochloric Acid → Pivaloyloxymethyl 1-[(2'-carboxybiphenyl-4-yl)methyl]-4-(1-hydroxy-1-methylethyl)-2-propylimidazole-5-carboxylate

HRID 52903Notes

Reaction equation

HRID 52903 reaction equation
[C:1]([O:7][CH2:8][O:9][C:10]([C:12]1[N:16]([CH2:17][C:18]2[CH:23]=[CH:22][C:21]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=3[C:30]([O:32]C(C)(C)C)=[O:31])=[CH:20][CH:19]=2)[C:15]([CH2:37][CH2:38][CH3:39])=[N:14][C:13]=1[C:40]([OH:43])([CH3:42])[CH3:41])=[O:11])(=[O:6])[C:2]([CH3:5])([CH3:4])[CH3:3].Cl>O1CCOCC1>[C:30]([C:25]1[CH:26]=[CH:27][CH:28]=[CH:29][C:24]=1[C:21]1[CH:20]=[CH:19][C:18]([CH2:17][N:16]2[C:12]([C:10]([O:9][CH2:8][O:7][C:1](=[O:6])[C:2]([CH3:5])([CH3:4])[CH3:3])=[O:11])=[C:13]([C:40]([OH:43])([CH3:42])[CH3:41])[N:14]=[C:15]2[CH2:37][CH2:38][CH3:39])=[CH:23][CH:22]=1)([OH:32])=[O:31]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 10579348Pivaloyloxymethyl 1-[(2'-t-butoxycarbonylbiphenyl-4-yl)methyl]-4-(1-hydroxy-1-methylethyl)-2-propylimidazole-5-carboxylate

Product 1

HCID 10816196Pivaloyloxymethyl 1-[(2'-carboxybiphenyl-4-yl)methyl]-4-(1-hydroxy-1-methylethyl)-2-propylimidazole-5-carboxylateYield 109.1%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A mixture of 6.6 g of pivaloyloxymethyl-1-[(2'-t-butoxycarbonylbiphenyl-4-yl)methyl]-4-(1-hydroxy-1-methylethyl)-2-propylimidazole-5-carboxylate [prepared as described in step (c) above] and 57 ml of a 4N solution of hydrogen chloride in dioxane was stirred at room temperature for 4 hours. At the end of this time, the reaction mixture was concentrated by evaporation under reduced pressure, and the residue was triturated with ethyl acetate to crystallize it, giving 6.52 g of the title compound as the hydrochloride, melting at 170°-173° C.

Workup

  1. concentrationAt the end of this time, the reaction mixture was concentrated by evaporation under reduced pressure
  2. customthe residue was triturated with ethyl acetate
  3. customto crystallize it

Sources & evidence

ORD record
ord-7e5960c71bd44e2c89c5df1e2f41dd26
Source dataset
uspto-grants-1997_04
Patent number
US05616599

Reaction notes

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