Methanol → HCID 44159407, compound

HRID 1919945Notes

Reaction equation

HRID 1919945 reaction equation
C[O:2][C:3](=[O:33])[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:30](=[O:32])[CH3:31])[CH2:25][C:26]([CH3:29])([CH3:28])[CH3:27])[C:8]([O:11][CH3:12])=[CH:9][CH:10]=1.CO.[OH-].[Na+]>C1COCC1.C(Cl)Cl.Cl>[C:30]([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:33])=[O:2])[CH:6]=1)[CH2:25][C:26]([CH3:28])([CH3:29])[CH3:27])(=[O:32])[CH3:31]

Participants

7

Reactant 3

HCID 887MethanolHCID 14798Sodium HydroxideHCID 66603723HCID 66603723, compound

Product 1

HCID 44159407HCID 44159407, compound

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolventHCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

(2′-{[Acetyl-(2,2-dimethyl-propyl)-amino]-methyl}-6-methoxy-4′-trifluoromethyl-biphenyl-3-acetic acid methyl ester (0.152 g, 0.33 mmol) was dissolved in THF (1.5 mL), MeOH (1.2 mL), and aqueous 1N NaOH (0.72 mL), and the mixture was stirred at room temperature for 4 hours. Once no starting material was seen by analytical LCMS, the mixture was diluted with CH2Cl2 and aqueous 1N HCl, and the aqueous layer was extracted with CH2Cl2. The combined organic layers were dried over MgSO4, filtered, and concentrated to give the title compound.

Workup

  1. extractionthe aqueous layer was extracted with CH2Cl2
  2. dry with materialThe combined organic layers were dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-2777d8a5797d4e4c9da1525315f97f83
Source dataset
uspto-grants-2012_05
Patent number
US08168678B2

Reaction notes

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