Methanol → HCID 11675146, compound

HRID 1754490Notes

Reaction equation

HRID 1754490 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 (MgS04) 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. customdried (MgS04)
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-355e015b9e6d48a59c08263c8be41843
Source dataset
uspto-grants-2015_10
Patent number
US09169251B2

Reaction notes

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