Ammonia → 1-[(2'-t-Butoxycarbonylbiphenyl-4-yl)methyl]-2-butyl-4-hydroxymethylimidazole-5-carboxamide

HRID 265083Notes

Reaction equation

HRID 265083 reaction equation
[NH3:1].[C:2]([O:6][C:7]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[C:15]1[CH:20]=[CH:19][C:18]([CH2:21][N:22]2[C:26]([C:27](ON3C(=O)CCC3=O)=[O:28])=[C:25]([CH2:37][OH:38])[N:24]=[C:23]2[CH2:39][CH2:40][CH2:41][CH3:42])=[CH:17][CH:16]=1)=[O:8])([CH3:5])([CH3:4])[CH3:3]>O1CCCC1>[C:2]([O:6][C:7]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[C:15]1[CH:16]=[CH:17][C:18]([CH2:21][N:22]2[C:26]([C:27]([NH2:1])=[O:28])=[C:25]([CH2:37][OH:38])[N:24]=[C:23]2[CH2:39][CH2:40][CH2:41][CH3:42])=[CH:19][CH:20]=1)=[O:8])([CH3:3])([CH3:5])[CH3:4]

Participants

4

Reactant 2

HCID 222AmmoniaHCID 19036239Succinimido 1-[(2'-t-butoxycarbonylbiphenyl-4-yl)methyl]-2-butyl-4-hydroxymethylimidazole-5-carboxylate

Product 1

HCID 190362801-[(2'-t-Butoxycarbonylbiphenyl-4-yl)methyl]-2-butyl-4-hydroxymethylimidazole-5-carboxamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

0.5 ml of concentrated aqueous ammonia was added to a solution of 0.60 g of succinimido 1-[(2'-t-butoxycarbonylbiphenyl-4-yl)methyl]-2-butyl-4-hydroxymethylimidazole-5-carboxylate [prepared as described in step (a) above] in 6 ml of tetrahydrofuran, and the title compound started to separate immediately. The solvent was removed by distillation under reduced pressure, and the resulting residue was washed with diethyl ether and with water, to afford 0.38 g of the title compound as a powder, melting at 222°-224° C.

Sources & evidence

ORD record
ord-d13ea6834a154106a162bd45c55b189d
Source dataset
uspto-grants-1997_07
Patent number
US05646171

Reaction notes

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