N-Hydroxysuccinimide → Succinimido 1-[(2'-t-Butoxycarbonylbiphenyl-4-yl)methyl)-4-(1-hydroxy-2,2-dimethylpropyl)-2-propylimidazole-5-carboxylate

HRID 52953Notes

Reaction equation

[C:1]([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]([OH:28])=[O:27])=[C:24]([CH:29]([OH:34])[C:30]([CH3:33])([CH3:32])[CH3:31])[N:23]=[C:22]2[CH2:35][CH2:36][CH3:37])=[CH:16][CH:15]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].O[N:39]1[C:43](=[O:44])[CH2:42][CH2:41][C:40]1=[O:45]>>[C:1]([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][N:39]3[C:43](=[O:44])[CH2:42][CH2:41][C:40]3=[O:45])=[O:27])=[C:24]([CH:29]([OH:34])[C:30]([CH3:33])([CH3:32])[CH3:31])[N:23]=[C:22]2[CH2:35][CH2:36][CH3:37])=[CH:16][CH:15]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

Reactant 2

HCID 80170N-Hydroxysuccinimide

HCID 190361161-[(2'-t-Butoxycarbonylbiphenyl-4-yl)methyl]-4-(1-hydroxy-2,2-dimethylpropyl)-2-propylimidazole-5-carboxylic acid

Product 1

HCID 19036141Succinimido 1-[(2'-t-Butoxycarbonylbiphenyl-4-yl)methyl)-4-(1-hydroxy-2,2-dimethylpropyl)-2-propylimidazole-5-carboxylateYield 89.8%

Procedure

Following a procedure similar to that described in Example 52(a), but using 300 mg of 1-[(2'-t-butoxycarbonylbiphenyl-4-yl)methyl]-4-(1-hydroxy-2,2-dimethylpropyl)-2-propylimidazole-5-carboxylic acid [prepared as described in step (e) above], 110 mg of N-hydroxysuccinimide and 130 mg of N,N-dicyclohexylcarbodiimide, 321 mg of the title compound were obtained as an amorphous solid.

Sources & evidence

ORD record: ord-3dd5ad43cc1d45378ee7565caf7bcda3
Source dataset: uspto-grants-1997_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05616599

Reaction notes

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