Hydrochloric Acid → 3-(2-Methylsulfanylpyrimidin-4-yl)-4-oxo-4-(3-trifluoromethylphenyl)butyric Acid

HRID 394473Notes

Reaction equation

HRID 394473 reaction equation
C[O:2][C:3](=[O:26])[CH2:4][CH:5]([C:18]1[CH:23]=[CH:22][N:21]=[C:20]([S:24][CH3:25])[N:19]=1)[C:6](=[O:17])[C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([C:13]([F:16])([F:15])[F:14])[CH:8]=1.O1CCOCC1.Cl.CCCCCC>CCOCC>[CH3:25][S:24][C:20]1[N:19]=[C:18]([CH:5]([C:6](=[O:17])[C:7]2[CH:12]=[CH:11][CH:10]=[C:9]([C:13]([F:15])([F:14])[F:16])[CH:8]=2)[CH2:4][C:3]([OH:26])=[O:2])[CH:23]=[CH:22][N:21]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8058HexaneHCID 312751,4-DioxaneHCID 590837093-(2-Methylsulfanylpyrimidin-4-yl)-4-oxo-4-(3-trifluoromethylphenyl)butyric Acid Methyl Ester

Product 1

HCID 181766313-(2-Methylsulfanylpyrimidin-4-yl)-4-oxo-4-(3-trifluoromethylphenyl)butyric Acid

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A solution of Compound 4 (27.1 g, 64 mmol) and dioxane (500 mL) were stirred under argon. Hydrochloric acid (6N, 250 mL) was added dropwise using an addition funnel. After 3d dioxane was removed in vacuo. The remaining aqueous mixture was extracted exhaustively with methylene chloride. The combined organic extracts were dried over anhydrous sodium sulfate then the solvent was removed in vacuo to give a yellow oil. Hexane followed by ether was added to afford a solid (5) which was isolated by vacuum filtration: 18.6 g (50.4 mmol, 79%)

Workup

  1. customAfter 3d dioxane was removed in vacuo
  2. extractionThe remaining aqueous mixture was extracted exhaustively with methylene chloride
  3. dry with materialThe combined organic extracts were dried over anhydrous sodium sulfate
  4. customthe solvent was removed in vacuo
  5. customto give a yellow oil
  6. additionwas added

Sources & evidence

ORD record
ord-04b3fb150d244be0b587de9870a81c57
Source dataset
uspto-grants-2003_08
Patent number
US06602872B1

Reaction notes

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