Ethyl Acetate → HCID 22618752, compound

HRID 842294Notes

Reaction equation

HRID 842294 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][CH2:16][C:17]2([CH2:30][CH3:31])[CH2:21][O:20]C(=O)[N:18]2[C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O.[OH-].[Li+].C(OCC)(=O)C>CO.O>[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][CH2:16][C:17]([NH:18][C:23]([O:25][C:26]([CH3:27])([CH3:29])[CH3:28])=[O:24])([CH2:30][CH3:31])[CH2:21][OH:20])=[CH:11][CH:10]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 8857Ethyl AcetateHCID 168937Lithium hydroxide, monohydrateHCID 22618758HCID 22618758, compound

Product 1

HCID 22618752HCID 22618752, compoundYield 142%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a solution of 4-(2-(4-benzyloxyphenyl)ethyl)-3-tert-butoxycarbonyl-4-ethyloxazolidin-2-one (18 g) in methanol (432 ml) was added a solution of lithium hydroxide monohydrate (9.1 g) in water (50 ml) and the mixture was stirred at room temperature for 3 hours. Ethyl acetate was added to the reaction mixture and the mixture was washed with water and a saturated brine and dried over anhydrous sodium sulfate. The solvent was distilled away under reduced pressure to give the subject compound (24 g).

Workup

  1. washthe mixture was washed with water
  2. dry with materiala saturated brine and dried over anhydrous sodium sulfate
  3. distillationThe solvent was distilled away under reduced pressure

Sources & evidence

ORD record
ord-3d59fdf045b645c08cd7429237d86270
Source dataset
uspto-grants-2002_04
Patent number
US06372800B1

Reaction notes

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