Methanol → HCID 44159296, compound

HRID 1810228Notes

Reaction equation

HRID 1810228 reaction equation
C[O:2][C:3](=[O:29])[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:26](=[O:28])[CH3:27])[CH3:25])[C:8]([O:11][CH3:12])=[CH:9][CH:10]=1.CO.[OH-].[Na+]>C1COCC1.C(Cl)Cl.O>[C:26]([N:24]([CH2:23][C:14]1[CH:15]=[C:16]([C:19]([F:20])([F:22])[F:21])[CH:17]=[CH:18][C:13]=1[C:7]1[C:8]([O:11][CH3:12])=[CH:9][CH:10]=[C:5]([CH2:4][C:3]([OH:29])=[O:2])[CH:6]=1)[CH3:25])(=[O:28])[CH3:27]

Participants

7

Reactant 3

HCID 887MethanolHCID 14798Sodium HydroxideHCID 66604246HCID 66604246, compound

Product 1

HCID 44159296HCID 44159296, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

{2′-[(Acetyl-methyl-amino)-methyl]-6-methoxy-4′-trifluoromethyl-biphenyl-3-yl}-acetic acid methyl ester (0.038 g, 0.09 mmol) was dissolved in THF (0.38 mL), MeOH (0.3 mL), and aqueous 1N NaOH (0.2 mL), and the mixture was stirred at room temperature for 1 hour. Once no starting material was seen by analytical LCMS, the mixture was diluted with CH2Cl2 and H2O, and the aqueous layer was extracted with CH2Cl2. The combined organic layers were dried over MgSO4, filtered, and concentrated, and the residue was purified by preparative HPLC. The desired fractions were combined, concentrated, and the isolated material was diluted with CH2Cl2 and neutralized with saturated aqueous NaHCO3. The organic layer was separated, dried over MgSO4, filtered, and concentrated to give the title compound. The aqueous layer was acidified and extracted with EtOAc, and the organic layer was concentrated to give additional product. M+H is 396.

Workup

  1. extractionthe aqueous layer was extracted with CH2Cl2
  2. dry with materialThe combined organic layers were dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customthe residue was purified by preparative HPLC
  6. concentrationconcentrated
  7. additionthe isolated material was diluted with CH2Cl2 and neutralized with saturated aqueous NaHCO3
  8. customThe organic layer was separated
  9. dry with materialdried over MgSO4
  10. filtrationfiltered
  11. concentrationconcentrated

Sources & evidence

ORD record
ord-83b8d5e020c749fb8482644a319f018c
Source dataset
uspto-grants-2013_01
Patent number
US08362044B2

Reaction notes

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