Water → HCID 57570907, compound

HRID 1695325Notes

Reaction equation

HRID 1695325 reaction equation
[F:1][C:2]([F:8])([F:7])[S:3](Cl)(=[O:5])=[O:4].[OH2:9].[C:10]([O:13][CH2:14][CH3:15])(=[O:12])[CH3:11].[N:16]1[CH:21]=[CH:20][CH:19]=[CH:18]C=1>>[CH2:14]([O:13][C:10]([C:11]1[CH:18]=[C:19]([O:4][S:3]([C:2]([F:8])([F:7])[F:1])(=[O:9])=[O:5])[CH:20]=[C:21]([C:10]([O:13][CH2:14][CH3:15])=[O:12])[N:16]=1)=[O:12])[CH3:15]

Participants

5

Reactant 4

HCID 962WaterHCID 1049PyridineHCID 8857Ethyl AcetateHCID 79000Trifluoromethanesulfonyl chloride

Product 1

HCID 57570907HCID 57570907, compound

Procedure

To a cooled (0° C.) solution of chelidamic acid diethyl ester (Chaubet, F.; Nguyen van duong, M.; Gref, A.; Courtieu, J.; Crumbliss, A. L.; Gaudemer, A. Tetrahedron Lett. 1990, 31(40), 5729-5732) (3.5 g) in pyridine (35 mL), was added dropwise trifluoromethanesulfonyl chloride (2.6 mL). The reaction was then stirred at room temperature for 3 hours. Water and ethyl acetate were added. The layers were separated, and the aqueous layer was extracted twice ethyl acetate. The combined organic solutions were dried over magnesium sulfate, and concentrated in vacuo to a residue. The residue was purified by silica gel chromatography (Merck SuperVarioPrep 90g column, Si60 15-40μm), eluted with dichloromethane to give 4-trifluoromethanesulfonyloxy-pyridine-2,6-dicarboxylic acid diethyl ester (4.2g).

Workup

  1. customThe layers were separated
  2. extractionthe aqueous layer was extracted twice ethyl acetate
  3. dry with materialThe combined organic solutions were dried over magnesium sulfate
  4. concentrationconcentrated in vacuo to a residue
  5. customThe residue was purified by silica gel chromatography (Merck SuperVarioPrep 90g column, Si60 15-40μm)
  6. washeluted with dichloromethane

Sources & evidence

ORD record
ord-217e5025c4924e4e827770bb5d4b6413
Source dataset
uspto-grants-2012_04
Patent number
US08163736B2

Reaction notes

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