Methanol → HCID 66673048, compound

HRID 422923Notes

Reaction equation

HRID 422923 reaction equation
[CH3:1][C@@:2]1([CH2:8][CH2:9][C:10]2[NH:11][C:12]([C:15](=[O:26])[CH2:16][CH2:17][CH2:18][CH2:19][C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)=[CH:13][CH:14]=2)[CH2:6][O:5]C(=O)[NH:3]1.CO.O1CCCC1.[OH-].[Na+]>O>[NH2:3][C@:2]([CH3:1])([CH2:8][CH2:9][C:10]1[NH:11][C:12]([C:15](=[O:26])[CH2:16][CH2:17][CH2:18][CH2:19][C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=2)=[CH:13][CH:14]=1)[CH2:6][OH:5]

Participants

6

Reactant 4

HCID 887MethanolHCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 66672866HCID 66672866, compound

Product 1

HCID 66673048HCID 66673048, compoundYield 79%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

To a solution of (4R)-4-methyl-4-{2-[5-(5-phenylpentanoyl)pyrrol-2-yl]ethyl}-1,3-oxazolidin-2-one (41.0 mg, 0.12 mmol) obtained in Example (42a) in a mixed solvent of methanol (2 ml), tetrahydrofuran (2 ml) and water (2 ml) was added 10N aqueous sodium hydroxide solution (0.12 ml, 1.17 mmol), and the resulting mixture was refluxed for 4 days. After cooling to room temperature, water was added to the reaction mixture, and the resulting mixture was extracted with ethyl acetate. The extract was washed with saturated aqueous sodium chloride solution and dried over anhydrous sodium sulfate. After filtration, the solvent was removed in vacuo, and the residue was purified by chromatography on a basic silica gel column (NH type) using a mixed solvent of dichloromethane and methanol (20:1) as the eluent to afford the title compound (30.0 mg, yield: 79%).

Workup

  1. temperaturethe resulting mixture was refluxed for 4 days
  2. extractionthe resulting mixture was extracted with ethyl acetate
  3. washThe extract was washed with saturated aqueous sodium chloride solution
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationAfter filtration
  6. customthe solvent was removed in vacuo
  7. customthe residue was purified by chromatography on a basic silica gel column (NH type)

Sources & evidence

ORD record
ord-596e6b78f660412db260139607c82b17
Source dataset
uspto-grants-2012_01
Patent number
US08101650B2

Reaction notes

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