tert-Butyl 4'-(bromomethyl)biphenyl-2-carboxylate → HCID 67708052, compound

HRID 265142Notes

Reaction equation

[OH:1][C:2]([C:5]1[N:6]=[C:7]([CH2:14][O:15][CH3:16])[NH:8][C:9]=1[C:10]([O:12][CH3:13])=[O:11])([CH3:4])[CH3:3].[CH3:17]C(C)([O-])C.[K+].[C:23]([O:27][C:28]([C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=1[C:36]1[CH:43]=[CH:42][C:39](CBr)=[CH:38][CH:37]=1)=[O:29])([CH3:26])([CH3:25])[CH3:24]>>[C:23]([O:27][C:28]([C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=1[C:36]1[CH:43]=[CH:42][C:39]([N:8]2[C:9]([C:10]([O:12][CH3:13])=[O:11])=[C:5]([C:2]([OH:1])([CH3:3])[CH3:4])[NH:6][C:7]2([CH3:17])[CH2:14][O:15][CH3:16])=[CH:38][CH:37]=1)=[O:29])([CH3:26])([CH3:24])[CH3:25]

Participants

Reactant 3

HCID 9906257tert-Butyl 4'-(bromomethyl)biphenyl-2-carboxylate

HCID 23665647Potassium tert-butoxide

HCID 178494672Methyl 4-(1-hydroxy-1-methylethyl)-2-methoxymethylimidazole-5-carboxylate

Product 1

HCID 67708052HCID 67708052, compoundYield 93.5%

Procedure

Following a procedure similar to that described in Example82(a), but using 230 mg of methyl 4-(1-hydroxy-1-methylethyl)-2-methoxymethylimidazole-5-carboxylate [prepared as described in Preparation 42(v)], 119 mg of potassium t-butoxide and 420 mg of 4-[2-(t-butoxycarbonyl)phenyl]benzyl bromide and then purifying the product by column chromatography through silica gel using a 1:2 by volume mixture of hexane and ethyl acetate as the eluent, 468 mg of the title compound were obtained as a syrup.

Workup

custompurifying the product by column chromatography through silica gel using a 1:2
additionby volume mixture of hexane and ethyl acetate as the eluent

Sources & evidence

ORD record: ord-03c2d4170d7b4c328266ccb61b4dddd5
Source dataset: uspto-grants-1997_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05646171

Reaction notes

Loading…