Potassium tert-butoxide → Ethyl 1-[(2'-t-butoxycarbonylbiphenyl-4-yl)methyl]-4-(1-hydroxy-1-methylethyl)-2-propylimidazole-5-carboxylate

HRID 52966Notes

Reaction equation

HRID 52966 reaction equation
[OH:1][C:2]([C:5]1[N:6]=[C:7]([CH2:15][CH2:16][CH3:17])[NH:8][C:9]=1[C:10]([O:12][CH2:13][CH3:14])=[O:11])([CH3:4])[CH3:3].Br[CH2:19][C:20]1[CH:25]=[CH:24][C:23]([C:26]2[C:27]([C:32]([O-:34])=[O:33])=[CH:28][CH:29]=[CH:30][CH:31]=2)=[CH:22][CH:21]=1.[CH3:35][C:36]([CH3:39])([O-])[CH3:37].[K+]>>[C:36]([O:34][C:32]([C:27]1[CH:28]=[CH:29][CH:30]=[CH:31][C:26]=1[C:23]1[CH:24]=[CH:25][C:20]([CH2:19][N:8]2[C:9]([C:10]([O:12][CH2:13][CH3:14])=[O:11])=[C:5]([C:2]([OH:1])([CH3:4])[CH3:3])[N:6]=[C:7]2[CH2:15][CH2:16][CH3:17])=[CH:21][CH:22]=1)=[O:33])([CH3:39])([CH3:37])[CH3:35]

Participants

4

Reactant 3

HCID 23665647Potassium tert-butoxideHCID 516686704'-Bromomethylbiphenyl-2-carboxylateHCID 178440079HCID 178440079, compound

Product 1

HCID 10625404Ethyl 1-[(2'-t-butoxycarbonylbiphenyl-4-yl)methyl]-4-(1-hydroxy-1-methylethyl)-2-propylimidazole-5-carboxylateYield 74.1%

Procedure

Following a procedure similar to that described in Example 68(a), but using 4.80 g of ethyl 4-(1-hydroxy-1-methylethyl)-2-propylimidazole-5-carboxylate (prepared as described in Preparation 9), 6.94 g of t-buryl 4'-bromomethylbiphenyl-2-carboxylate and 2.28 g of potassium t-butoxide, 7.50 g of the title compound were obtained as crystals, melting at 90°-91° C.

Sources & evidence

ORD record
ord-bae8d0e7e0024f5884664ba9c7d8e283
Source dataset
uspto-grants-1997_04
Patent number
US05616599

Reaction notes

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