Lithium Hydroxide → HCID 67763268, compound

HRID 1082193Notes

Reaction equation

HRID 1082193 reaction equation
[OH-].[Li+].[C:3]([O:7][C:8]([N:10]1[C@@H:14]([CH:15]2[CH2:17][CH2:16]2)[CH:13]([C:18]([O:20]CC)=[O:19])[O:12][CH:11]1[C:23]1[CH:28]=[CH:27][C:26]([O:29][CH3:30])=[CH:25][CH:24]=1)=[O:9])([CH3:6])([CH3:5])[CH3:4]>CO.O>[C:3]([O:7][C:8]([N:10]1[C@@H:14]([CH:15]2[CH2:17][CH2:16]2)[CH:13]([C:18]([OH:20])=[O:19])[O:12][CH:11]1[C:23]1[CH:28]=[CH:27][C:26]([O:29][CH3:30])=[CH:25][CH:24]=1)=[O:9])([CH3:6])([CH3:5])[CH3:4]

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 86750106HCID 86750106, compound

Product 1

HCID 67763268HCID 67763268, compoundYield 125.5%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

(1)Ethyl (45, 5R)-3-tert-butoxycarbonyl-2-(4-methoxyphenyl)-4-cyclopropyl-5-oxazolidinecarboxylate (diastereomeric mixture) obtained in Example 6(1) is purified by column chromatography to give ethyl (4S,5R)-3-tert-butoxycarbonyl-2-(4-methoxyphenyl)-4-cyclopropyl-5-oxazolidinecarboxylate. A 87 mg of lithium hydroxide is added under ice-cooling to a solution of 1.03 g of ethyl (4S,SR)-3-tert-butoxycarbonyl-2-(4-methoxyphenyl)-4-cyclopropyl-5-oxazolidinecarboxylate in a mixture of 20 ml of methanol and 10 ml of water. The mixture is stirred at room temperature for 30 minutes. The reaction n-tixture is evaporated under reduced pressure to remove methanol. The pH of the solution of the residue in ethyl acetate is adjusted to pH 2 with 1N hydrochloric acid under ice-cooling. After the mixture is extracted with ethyl acetate, the extract is washed with brine, dried and evaporated to remove the solvent to give 1.20 g of (4S,SR)-3-tert-butoxycarbonyl-2-(4-methoxyphenyl)-4-cyclopropyl-5-oxazolidinecarboxylic acid quantitatively.

Workup

  1. customThe reaction n-tixture is evaporated under reduced pressure
  2. customto remove methanol
  3. temperaturecooling
  4. extractionAfter the mixture is extracted with ethyl acetate
  5. washthe extract is washed with brine
  6. customdried
  7. customevaporated
  8. customto remove the solvent

Sources & evidence

ORD record
ord-e902a12fb1b047a882acd5219da9a42b
Source dataset
uspto-grants-1996_12
Patent number
US05589502

Reaction notes

Loading…