Methanol → HCID 11675146, compound

HRID 1254888Notes

Reaction equation

HRID 1254888 reaction equation
C[O:2][C:3](=[O:27])[CH2:4][C:5]1[C:13]2[C:8](=[N:9][CH:10]=[CH:11][CH:12]=2)[N:7]([CH:14]([C:16]2[CH:21]=[CH:20][C:19]([S:22]([CH3:25])(=[O:24])=[O:23])=[CH:18][CH:17]=2)[CH3:15])[C:6]=1[CH3:26].CO.[OH-].[Li+]>C1COCC1>[CH3:25][S:22]([C:19]1[CH:20]=[CH:21][C:16]([CH:14]([N:7]2[C:8]3=[N:9][CH:10]=[CH:11][CH:12]=[C:13]3[C:5]([CH2:4][C:3]([OH:27])=[O:2])=[C:6]2[CH3:26])[CH3:15])=[CH:17][CH:18]=1)(=[O:23])=[O:24]

Participants

5

Reactant 3

HCID 887MethanolHCID 3939Lithium HydroxideHCID 67219209HCID 67219209, compound

Product 1

HCID 11675146HCID 11675146, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of {1-[1-(4-methanesulfonyl-phenyl)-ethyl]-2-methyl-1H-pyrrolo[2,3-b]pyridin-3-yl}-acetic acid methyl ester (Enantiomer A) (22 mg, 0.05 mmol) in THF (0.5 ml) and methanol (0.5 ml) is treated with 2M lithium hydroxide (0.2 ml) and stirred at room temperature for 30 minutes. The solvent is removed in vacuo and the crude is dissolved in water (10 ml) and acidified to pH1 using concentrated HCl. The mixture is then extracted with ethyl acetate (2×10 ml) and the organic portions are washed with brine, dried (MgSO4) and concentrated in vacuo to yield the titled product as a colourless glassy solid. (MH+ 373) The enantiomer of the titled compound (Enantiomer 2) is prepared analogously using the procedure described above by replacing Enantiomer A with Enantiomer B. (MH+ 373)

Workup

  1. customThe solvent is removed in vacuo
  2. dissolutionthe crude is dissolved in water (10 ml)
  3. extractionThe mixture is then extracted with ethyl acetate (2×10 ml)
  4. washthe organic portions are washed with brine
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-e7129f32d1a9461080bff3740dd78a08
Source dataset
uspto-grants-2013_06
Patent number
US08455645B2

Reaction notes

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