Pyrrolidine → Tert-butyl 6-[({2'-cyano-4'-[(methoxycarbonyl)methyl]-1,1'-biphenyl-4-yl}oxy)methyl]-2-hydroxy-3-(trifluoromethyl)benzoate

HRID 2076660Notes

Reaction equation

N1CCCC1.C(OC([O:13][C:14]1[C:26]([C:27]([F:30])([F:29])[F:28])=[CH:25][CH:24]=[C:23]([CH2:31][O:32][C:33]2[CH:38]=[CH:37][C:36]([C:39]3[CH:44]=[CH:43][C:42]([CH2:45][C:46]([O:48][CH3:49])=[O:47])=[CH:41][C:40]=3[C:50]#[N:51])=[CH:35][CH:34]=2)[C:15]=1[C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])=O)(C)(C)C>O1CCOCC1>[C:50]([C:40]1[CH:41]=[C:42]([CH2:45][C:46]([O:48][CH3:49])=[O:47])[CH:43]=[CH:44][C:39]=1[C:36]1[CH:37]=[CH:38][C:33]([O:32][CH2:31][C:23]2[C:15]([C:16]([O:18][C:19]([CH3:20])([CH3:21])[CH3:22])=[O:17])=[C:14]([OH:13])[C:26]([C:27]([F:28])([F:29])[F:30])=[CH:25][CH:24]=2)=[CH:34][CH:35]=1)#[N:51]

Participants

Conditions

Temperature: 50 °C

Procedure

Pyrrolidine (33 μl, 0.39 mmol) was added to a solution of crude tert-butyl 2-[(tert-butoxycarbonyl)oxy]-6-[({2′-cyano-4′-[(methoxycarbonyl)methyl]-1,1′-biphenyl-4-yl}oxy)methyl]-3-(trifluoromethyl)benzoate (125 mg) obtained in the above in 1,4-dioxane (4 ml), and the mixture was stirred at 50° C. for 2 hours. The residue obtained by removing the solvent under reduced pressure was purified by silica gel preparative thin layer chromatography (developing solvent: n-hexane/ethyl acetate=5/1) to give tert-butyl 6-[({2′-cyano-4′-[(methoxycarbonyl)methyl]-1,1′-biphenyl-4-yl}oxy)methyl]-2-hydroxy-3-(trifluoromethyl)benzoate (100 mg, 60%).

Workup

customThe residue obtained
customby removing the solvent under reduced pressure
customwas purified by silica gel preparative thin layer chromatography (developing solvent: n-hexane/ethyl acetate=5/1)

Sources & evidence

ORD record: ord-914258f031d14e9d84a9f9206cb97e88
Source dataset: uspto-grants-2011_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07923573B2

Reaction notes

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