Water → HCID 86629103, compound

HRID 333802Notes

Reaction equation

HRID 333802 reaction equation
[CH2:1]([O:3][C:4](=[O:34])[CH:5]([CH2:11][C:12]1[CH:17]=[CH:16][C:15]([CH:18]([CH3:32])[C:19]([C:25]2[CH:30]=[CH:29][N:28]=[C:27]([Cl:31])[CH:26]=2)([OH:24])[C:20]([F:23])([F:22])[F:21])=[C:14]([Cl:33])[CH:13]=1)C(OCC)=O)[CH3:2].[Na+].[Cl-].O>CS(C)=O>[CH2:1]([O:3][C:4](=[O:34])[CH2:5][CH2:11][C:12]1[CH:17]=[CH:16][C:15]([CH:18]([CH3:32])[C:19]([C:25]2[CH:30]=[CH:29][N:28]=[C:27]([Cl:31])[CH:26]=2)([OH:24])[C:20]([F:21])([F:23])[F:22])=[C:14]([Cl:33])[CH:13]=1)[CH3:2]

Participants

5

Reactant 3

HCID 962Water2×HCID 5234Sodium ChlorideHCID 86629104HCID 86629104, compound

Product 1

HCID 86629103HCID 86629103, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
140 °C

Procedure

To a mixture of 2-{3-chloro-4-[2-(2-chloro-pyridin-4-yl)-3,3,3-trifluoro-2-hydroxy-1-methyl-propyl]-benzyl}-malonic acid diethyl ester (214 mg) and NaCl (29 mg) in DMSO (4 mL) was added a small amount of water (0.011 mL). The mixture was then heated to 140° C. for 7 days. The mixture was poured into water and extracted with ethyl acetate. The organic extracts were washed with brine, 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, viscous oil (127 mg). MS (m/e)=450.1 (MH+).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic extracts were washed with brine
  3. dry with materialdried over Na2SO4
  4. customevaporated
  5. customThe residue was purified by flash chromatography (silica gel, gradient of ethyl acetate in heptane)

Sources & evidence

ORD record
ord-2cadce3859064c818d5cf118e4da7f75
Source dataset
uspto-grants-2014_11
Patent number
US08883786B2

Reaction notes

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