Sodium Hydroxide → 2-methyl-1-[(S)-1-(tetrahydro-furan-2-yl)methyl]-5-(2-trifluoromethoxy-phenyl)-1H-pyrrole-3-carboxylic acid

HRID 229861

Reaction equation

HRID 229861 reaction equation
C[O:2][C:3]([C:5]1[CH:9]=[C:8]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[O:16][C:17]([F:20])([F:19])[F:18])[N:7]([CH2:21][C@@H:22]2[CH2:26][CH2:25][CH2:24][O:23]2)[C:6]=1[CH3:27])=[O:4].[OH-].[Na+]>O1CCOCC1.O.C(OCC)C>[CH3:27][C:6]1[N:7]([CH2:21][C@@H:22]2[CH2:26][CH2:25][CH2:24][O:23]2)[C:8]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[O:16][C:17]([F:18])([F:20])[F:19])=[CH:9][C:5]=1[C:3]([OH:4])=[O:2]

Participants

6

Reactant 2

HCID 14798Sodium HydroxideHCID 690232432-methyl-1-[(S)-1-(tetrahydro-furan-2-yl)methyl]-5-(2-trifluoromethoxy-phenyl)-1H-pyrrole-3-carboxylic acid methyl ester

Product 1

HCID 690199812-methyl-1-[(S)-1-(tetrahydro-furan-2-yl)methyl]-5-(2-trifluoromethoxy-phenyl)-1H-pyrrole-3-carboxylic acidYield 93.5%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 3283Diethyl EtherSolventHCID 312751,4-DioxaneSolvent

Procedure

To a solution of 171 mg of 2-methyl-1-[(S)-1-(tetrahydro-furan-2-yl)methyl]-5-(2-trifluoromethoxy-phenyl)-1H-pyrrole-3-carboxylic acid methyl ester in dioxane (4 ml) and water (4 ml) was added 1.3 ml of a 1N solution of sodium hydroxide. The reaction mixture was heated at reflux for 20 hours. After such time the reaction mixture was allowed to cool down to room temperature. The mixture was diluted with diethyl ether and extracted with 1N sodium hydroxide solution. Water phases were pooled, acidified with 2N solution of hydrochloride acid and extracted twice with diethyl ether. The organic phases were pooled, washed with brine and dried with MgSO4. Solvent was removed to give 154 mg of the title compound as brownish oil; MS (ISP) 368.0 (M−H).

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux for 20 hours
  3. extractionextracted with 1N sodium hydroxide solution
  4. extractionextracted twice with diethyl ether
  5. washwashed with brine
  6. dry with materialdried with MgSO4
  7. customSolvent was removed

Sources & evidence

ORD record
ord-5421a429daa2457c8c3e34ed94cd0749
Source dataset
uspto-grants-2009_07
Patent number
US07563910B2

Linked notes

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