Pyridine → HCID 57719926, compound

HRID 1985299Notes

Reaction equation

HRID 1985299 reaction equation
[OH:1][CH2:2][C:3]1[CH:4]=[C:5]([CH2:9][CH:10]([O:16][CH:17]([CH3:19])[CH3:18])[C:11]([O:13][CH2:14][CH3:15])=[O:12])[CH:6]=[CH:7][CH:8]=1.[F:20][C:21]([F:32])([F:31])[C:22]1[CH:27]=[CH:26][C:25]([N:28]=[C:29]=[O:30])=[CH:24][CH:23]=1.N1C=CC=CC=1>O1CCCC1>[CH:17]([O:16][CH:10]([CH2:9][C:5]1[CH:6]=[CH:7][CH:8]=[C:3]([CH2:2][O:1][C:29]([NH:28][C:25]2[CH:24]=[CH:23][C:22]([C:21]([F:20])([F:31])[F:32])=[CH:27][CH:26]=2)=[O:30])[CH:4]=1)[C:11]([O:13][CH2:14][CH3:15])=[O:12])([CH3:18])[CH3:19]

Participants

5

Reactant 3

HCID 1049PyridineHCID 737684-(Trifluoromethyl)phenyl isocyanateHCID 22926842HCID 22926842, compound

Product 1

HCID 57719926HCID 57719926, compoundYield 87.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A suspension in tetrahydrofuran (2.0 ml) containing 100 mg of ethyl 3-[3-(hydroxymethyl)phenyl]-2-isopropoxypropanoate, 150 mg of α,α,α-trifluoro-p-tolylisocyanate and 35 μl of pyridine was stirred at room temperature for 14 hours. The solvent was removed, and the residue was treated with dichloromethane. After filtering off insoluble substances, the residue was purified by silica gel column chromatography, to give 149 mg of the title compound.

Workup

  1. customThe solvent was removed
  2. additionthe residue was treated with dichloromethane
  3. filtrationAfter filtering off insoluble substances
  4. customthe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-025c1fd1eca54d7bbe671f8bc96a9de1
Source dataset
uspto-grants-2009_06
Patent number
US07544835B2

Reaction notes

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