Sodium Hydroxide → 2-Hydroxy-N-[2-(2-methyl-7,8-dihydro-6H-indeno[5,4-d][1,3]oxazol-8-yl)ethyl]propanamide

HRID 1661437Notes

Reaction equation

HRID 1661437 reaction equation
C([O:4][CH:5]([CH3:24])[C:6]([NH:8][CH2:9][CH2:10][CH:11]1[C:22]2[C:21]3[O:20][C:19]([CH3:23])=[N:18][C:17]=3[CH:16]=[CH:15][C:14]=2[CH2:13][CH2:12]1)=[O:7])(=O)C.[OH-].[Na+]>O1CCCC1>[OH:4][CH:5]([CH3:24])[C:6]([NH:8][CH2:9][CH2:10][CH:11]1[C:22]2[C:21]3[O:20][C:19]([CH3:23])=[N:18][C:17]=3[CH:16]=[CH:15][C:14]=2[CH2:13][CH2:12]1)=[O:7]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 577812671-Methyl-2-{[2-(2-methyl-7,8-dihydro-6H-indeno[5,4-d][1,3]oxazol-8-yl)ethyl]amino}-2-oxoethyl Acetate

Product 1

HCID 577812182-Hydroxy-N-[2-(2-methyl-7,8-dihydro-6H-indeno[5,4-d][1,3]oxazol-8-yl)ethyl]propanamideYield 86%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 1-methyl-2-{[2-(2-methyl-7,8-dihydro-6H-indeno[5,4-d][1,3]oxazol-8-yl)ethyl]amino}-2-oxoethyl acetate (70 mg, 0.212 mmol) in tetrahydrofuran (2 mL) was added 1N aqueous sodium hydroxide solution (2 mL), and the mixture was stirred at room temperature for 2 hr. The solvent was evaporated under reduced pressure. The residue was diluted with ethyl acetate, washed with saturated brine and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (methanol/ethyl acetate) to give the title compound (52.4 mg, yield 86%).

Workup

  1. customThe solvent was evaporated under reduced pressure
  2. additionThe residue was diluted with ethyl acetate
  3. washwashed with saturated brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. customThe solvent was evaporated under reduced pressure
  6. customthe residue was purified by silica gel column chromatography (methanol/ethyl acetate)

Sources & evidence

ORD record
ord-ff5e887ff0624815bd1cd2285fc450fc
Source dataset
uspto-grants-2011_10
Patent number
US08030337B2

Reaction notes

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