Lithium Hydroxide → HCID 54210532, compound

HRID 975282Notes

Reaction equation

HRID 975282 reaction equation
[OH-].[Li+].[C:3]([O:7][C:8]([N:10]1[C@@H:14]([CH:15]2[CH2:17][CH2:16]2)[C@H: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)[C@H: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 53715740ethyl (4S,5R)-3-tert-butoxycarbonyl-2-(4-methoxyphenyl)-4-cyclopropyl-5-oxazolidinecarboxylate

Product 1

HCID 54210532HCID 54210532, compoundYield 125.5%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

(1)Ethyl (4S,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,5R)-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 mixture 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,5R)-3-tert-butoxycarbonyl-2-(4-methoxyphenyl)-4-cyclopropyl-5-oxazolidinecarboxylic acid quantitatively. ESI-MS(m/z): 386(M+ +Na) IR(neat,cm-1): 3080,1755,1702

Workup

  1. customThe reaction mixture 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-7af04c76b23b46b1a48503ed9560d440
Source dataset
uspto-grants-1997_03
Patent number
US05608073

Reaction notes

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