Carbon Dioxide → HCID 136166971, compound

HRID 1617499Notes

Reaction equation

Br[C:2]1[CH:3]=[C:4]([CH:8]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH2:9]/[C:10](/[C:13]2[CH:18]=[CH:17][N:16]=[CH:15][CH:14]=2)=[N:11]\[OH:12])[CH:5]=[CH:6][CH:7]=1.[C:25](=[O:27])=[O:26]>C1COCC1>[OH:12]/[N:11]=[C:10](/[C:13]1[CH:18]=[CH:17][N:16]=[CH:15][CH:14]=1)\[CH2:9][CH:8]([C:4]1[CH:3]=[C:2]([CH:7]=[CH:6][CH:5]=1)[C:25]([OH:27])=[O:26])[C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1

Participants

Conditions

Temperature: 0 °C

Procedure

At −78° C., to a solution of (E)-3-(3-bromo-phenyl)-3-phenyl-1-pyridin-4-yl-propan-1-one oxime (60 mg, example 12) in THF (1.5 mL) n-BuLi (1.6 M in hexane, 0.11 mL) was added dropwise. After stirring for 30 mins at that temperature carbon dioxide gas was bubbled into the solution for 5 min at −78° C. The reaction mixture was then warmed up to 0° C. and stirred for 15 min. The reaction was quenched by adding 1N aqueous KHSO4 solution, the phases were separated and the inorganic one was extracted with EtOAc (2×). The combined organic layers were washed with brine, dried over Na2SO4, filtered and concentrated in vacuo. Column chromatography on silica gel (CH2Cl2/MeOH 97:3) yielded 3-{3-[(E)-hydroxyimino]-1-phenyl-3-pyridin-4-yl-propyl}-benzoic acid (16 mg, 29%) as a yellow foam, MS (ESI+): m/z=347.1391 ([M+H]+).

Workup

customwas bubbled into the solution for 5 min at −78° C
customThe reaction was quenched
additionby adding 1N aqueous KHSO4 solution
customthe phases were separated
extractionthe inorganic one was extracted with EtOAc (2×)
washThe combined organic layers were washed with brine
dry with materialdried over Na2SO4
filtrationfiltered
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-354810192c3048259a62b7987e19acb3
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08765730B2

Reaction notes

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