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

HRID 52942

Reaction equation

HRID 52942 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-d7d3d0c0261641ea911bd0ed72151b20
Source dataset
uspto-grants-1997_04
Patent number
US05616599

Linked notes

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