Hydrochloric Acid → (2'-Aminomethyl-6-methoxy-4'-trifluoromethyl-biphenyl-3-yl)-acetic acid

HRID 563614Notes

Reaction equation

HRID 563614 reaction equation
C[O:2][C:3](=[O:25])[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][NH2:24])[C:8]([O:11][CH3:12])=[CH:9][CH:10]=1.[OH-].[Na+].Cl>C1COCC1.CO>[NH2:24][CH2:23][C:14]1[CH:15]=[C:16]([C:19]([F:22])([F:21])[F:20])[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:25])=[O:2])[CH:6]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium Hydroxide2×HCID 66607149(2'-Aminomethyl-6-methoxy-4'-trifluoromethyl-biphenyl-3-yl)-acetic acid methyl ester

Product 1

HCID 54673388(2'-Aminomethyl-6-methoxy-4'-trifluoromethyl-biphenyl-3-yl)-acetic acid

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

(2′-Aminomethyl-6-methoxy-4′-trifluoromethyl-biphenyl-3-yl)-acetic acid methyl ester (0.058 g, 0.17 mmol) in THF (0.59 mL) and MeOH (0.47 mL) was treated with 1N aqueous NaOH (0.17 mL, 0.17 mmol) and stirred overnight at room temperature. Analytical LCMS indicated that starting material was still present, so the reaction was stirred at 50° C. for 4.5 hours. Analytical LCMS showed that no change had occurred, so additional 1N aqueous NaOH (0.20 mL, 0.20 mmol) was added, and the reaction was stirred at 50° C. overnight. The mixture was cooled to room temperature and acidified with 1N aqueous HCl. The aqueous layer was extracted with CH2Cl2, and then diluted with brine and extracted twice with EtOAc. The combined organic layers were dried over MgSO4, filtered, and concentrated to give the title compound.

Workup

  1. stirringwas stirred at 50° C. for 4.5 hours
  2. stirringthe reaction was stirred at 50° C. overnight
  3. temperatureThe mixture was cooled to room temperature
  4. extractionThe aqueous layer was extracted with CH2Cl2
  5. additiondiluted with brine
  6. extractionextracted twice with EtOAc
  7. dry with materialThe combined organic layers were dried over MgSO4
  8. filtrationfiltered
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-a0713371597f426ea6675b02fd414a0a
Source dataset
uspto-grants-2011_11
Patent number
US08067445B2

Reaction notes

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