Methanol → HCID 24797825, compound

HRID 1512717Notes

Reaction equation

HRID 1512717 reaction equation
C[O:2][C:3](=[O:31])[CH2:4][CH2:5][O:6][C:7]1[CH:12]=[CH:11][C:10]([N:13]2[C:17]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)=[CH:16][C:15]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)=[C:14]2[CH3:30])=[CH:9][CH:8]=1.[Li+].[OH-].CO.O>C1COCC1>[CH3:30][C:14]1[N:13]([C:10]2[CH:9]=[CH:8][C:7]([O:6][CH2:5][CH2:4][C:3]([OH:31])=[O:2])=[CH:12][CH:11]=2)[C:17]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[CH:16][C:15]=1[C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 962WaterHCID 3939Lithium HydroxideHCID 24797826HCID 24797826, compound

Product 1

HCID 24797825HCID 24797825, compoundYield 18.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
40 °C

Procedure

A mixture of 3-[4-(2-methyl-3,5-diphenyl-pyrrol-1-yl)-phenoxy]-propionic acid methyl ester (51 mg; 0.12 mmol) and LiOH (5.4 mg; 0.23 mmol) in THF (1.0 mL)/MeOH (0.5 mL)/H2O (0.4 mL) was heated at 40° C. for 4 h then quenched with aq. citric acid. Product was extracted into EtOAc then washed with water and satd NaCl; then dried over MgSO4, filtered through silica with an EtOAc wash, concd then purified by MPLC (silica; 0-->100% EtOAc in hexanes gradient) yielding product as a grey solid (9 mg). 1H NMR (CDCl3) δ 7.53-7.48 (m, 2H), 7.41 (m, 2H), 7.24 (m, 1H), 7.20-7.08 (m, 7H), 6.91 (m, 2H), 6.55 (s, 1H), 4.27 (t, J=6.4 Hz, 2H), 2.89 (t, J=6.2 Hz, 2H), 2.23 (s, 3H).

Workup

  1. customthen quenched with aq. citric acid
  2. extractionProduct was extracted into EtOAc
  3. washthen washed with water
  4. dry with materialthen dried over MgSO4
  5. filtrationfiltered through silica with an EtOAc
  6. washwash
  7. customconcd then purified by MPLC (silica; 0-->100% EtOAc in hexanes gradient)

Sources & evidence

ORD record
ord-098bfb35f429467da334c13cd683fac4
Source dataset
uspto-grants-2012_07
Patent number
US08217073B2

Reaction notes

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