Hydrochloric Acid → HCID 66607706, compound

HRID 563502Notes

Reaction equation

HRID 563502 reaction equation
[CH3:1][O:2][C:3](=[O:30])[CH2:4][C:5]1[CH:6]=[C:7]([C:13]2[CH:18]=[CH:17][C:16]([C:19]([F:22])([F:21])[F:20])=[CH:15][C:14]=2[CH2:23][N:24]([C:27](=[O:29])[CH3:28])[CH2:25][CH3:26])[C:8]([O:11][CH3:12])=[CH:9][CH:10]=1.[OH-].[Na+].Cl.S(Cl)(Cl)=O.[C:38]([O-])(O)=O.[Na+]>CO.C1COCC1>[CH2:1]([O:2][C:3](=[O:30])[CH2:4][C:5]1[CH:6]=[C:7]([C:13]2[CH:18]=[CH:17][C:16]([C:19]([F:22])([F:21])[F:20])=[CH:15][C:14]=2[CH2:23][N:24]([C:27](=[O:29])[CH3:28])[CH2:25][CH3:26])[C:8]([O:11][CH3:12])=[CH:9][CH:10]=1)[CH3:38]

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 24386Thionyl ChlorideHCID 516892Sodium BicarbonateHCID 66604345HCID 66604345, compound

Product 1

HCID 66607706HCID 66607706, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To {2′-[(acetyl-ethyl-amino)-methyl]-6-methoxy-4′-trifluoromethyl-biphenyl-3-yl}-acetic acid methyl ester (0.292 g, 0.69 mmol) in MeOH (2.3 mL) and THF (2.9 mL) was added aqueous 1N NaOH (1.7 mL), and the solution was stirred at room temperature for 2 hours. The mixture was neutralized with aqueous 1N HCl, and the aqueous layer was separated and extracted with CH2Cl2. The combined organic layers were dried over MgSO4, filtered, and concentrated. The residue was dissolved in EtOH, and thionyl chloride (0.11 mL, 1.51 mmol) was added. The reaction was stirred for 30 minutes, until no starting material was seen by analytical LCMS. The solution was neutralized with saturated aqueous NaHCO3, and the aqueous layer was separated and extracted with CH2Cl2. The combined organic layers were washed with H2O, dried over MgSO4, filtered, and concentrated to give the title compound.

Workup

  1. customthe aqueous layer was separated
  2. extractionextracted with CH2Cl2
  3. dry with materialThe combined organic layers were dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. dissolutionThe residue was dissolved in EtOH
  7. stirringThe reaction was stirred for 30 minutes, until no starting material
  8. customthe aqueous layer was separated
  9. extractionextracted with CH2Cl2
  10. washThe combined organic layers were washed with H2O
  11. dry with materialdried over MgSO4
  12. filtrationfiltered
  13. concentrationconcentrated

Sources & evidence

ORD record
ord-2e13439870834f3fb7f94076f963bfd5
Source dataset
uspto-grants-2011_11
Patent number
US08067445B2

Reaction notes

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