Water → {3-Chloro-4-[2-(2-chloro-pyridin-4-yl)-3,3,3-trifluoro-2-hydroxy-1-methyl-propyl]-phenyl}-acetic acid

HRID 333801Notes

Reaction equation

[Cl:1][C:2]1[CH:3]=[C:4]([CH2:23][C:24]#N)[CH:5]=[CH:6][C:7]=1[CH:8]([CH3:22])[C:9]([C:15]1[CH:20]=[CH:19][N:18]=[C:17]([Cl:21])[CH:16]=1)([OH:14])[C:10]([F:13])([F:12])[F:11].[OH2:26].[OH-:27].[Na+]>Cl>[Cl:1][C:2]1[CH:3]=[C:4]([CH2:23][C:24]([OH:27])=[O:26])[CH:5]=[CH:6][C:7]=1[CH:8]([CH3:22])[C:9]([C:15]1[CH:20]=[CH:19][N:18]=[C:17]([Cl:21])[CH:16]=1)([OH:14])[C:10]([F:13])([F:12])[F:11]

Participants

Conditions

Temperature: 80 °C

Procedure

{3-Chloro-4-[2-(2-chloro-pyridin-4-yl)-3,3,3-trifluoro-2-hydroxy-1-methyl-propyl]-phenyl}-acetonitrile was suspended in aq. conc. HCl (3 mL) and stirred for 1 hour at 80° C. The mixture was allowed to cool and poured into water. The pH of the solution was adjusted to 6-7 with diluted NaOH. The aqueous layer was extracted three times with ethyl acetate and the extracts were dried over Na2SO4 and evaporated. The residue was purified by flash chromatography (silica gel, gradient of ethyl acetate in heptane) to give the title compound as a colorless solid (16 mg). MS (m/e)=408.1 (MH+).

Workup

temperatureto cool
extractionThe aqueous layer was extracted three times with ethyl acetate
dry with materialthe extracts were dried over Na2SO4
customevaporated
customThe residue was purified by flash chromatography (silica gel, gradient of ethyl acetate in heptane)

Sources & evidence

ORD record: ord-83b044d3b1a54ab89773af423836ce21
Source dataset: uspto-grants-2014_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08883786B2

Reaction notes

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