Hydrochloric Acid → HCID 57345399, compound

HRID 330746Notes

Reaction equation

HRID 330746 reaction equation
C[O:2][C:3]([C:5]1[C:10]([CH2:11][S:12]([CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=2[C:22]([F:25])([F:24])[F:23])(=[O:14])=[O:13])=[CH:9][CH:8]=[CH:7][N:6]=1)=O.O1CCCC1.Cl>C(OC(=O)C)C.C1CCCCC1>[O:14]=[S:12]1(=[O:13])[C:15]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=2[C:22]([F:23])([F:25])[F:24])=[C:3]([OH:2])[C:5]2=[N:6][CH:7]=[CH:8][CH:9]=[C:10]2[CH2:11]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 67983885HCID 67983885, compound

Product 1

HCID 57345399HCID 57345399, compoundYield 37.3%

Reagents, catalysts & solvents 1

HCID 21867204Cyclohexane ethylacetateSolvent

Procedure

To a solution of 3-(2-Trifluoromethyl-phenylmethanesulfonylmethyl)-pyridine-2-carboxylic acid methyl ester (7.58 g, 19.6 mmol) in tetrahydrofurane (160 ml) potassium tert-butoxide (2.20 g, 19.57 mmol) was added at room temperature and stirring was continued for 3.5 h. 1M HCl was added, diluted with methylenehloride and extracted. The organic phase was dried with sodiumsulfate and concentrated. Chromatography over silica with ethylacetate/cyclohexane gave 2.50 g colourless crystals (7.32 mmol).

Workup

  1. additiondiluted with methylenehloride
  2. extractionextracted
  3. dry with materialThe organic phase was dried with sodiumsulfate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-a04857228ba94c70b4842eaa912328b1
Source dataset
uspto-grants-2014_11
Patent number
US08877683B2

Reaction notes

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