Lithium Hydroxide → HCID 54210532, compound

HRID 975281Notes

Reaction equation

HRID 975281 reaction equation
[C:1]([O:5][C:6]([N:8]1[C@@H:12]([CH:13]2[CH2:15][CH2:14]2)[C@H:11]([C:16]([O:18]CC)=[O:17])[O:10][CH:9]1[C:21]1[CH:26]=[CH:25][C:24]([O:27][CH3:28])=[CH:23][CH:22]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[OH-].[Li+]>CO.O>[C:1]([O:5][C:6]([N:8]1[C@@H:12]([CH:13]2[CH2:15][CH2:14]2)[C@H:11]([C:16]([OH:18])=[O:17])[O:10][CH:9]1[C:21]1[CH:26]=[CH:25][C:24]([O:27][CH3:28])=[CH:23][CH:22]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

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 97%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a solution of 881 mg of ethyl (4S,5R)-3-tert-butoxycarbonyl-2-(4-methoxyphenyl)-4-cyclopropyl-5-oxazolidinecarboxylate (diastereomeric mixture) in 16 ml of methanol is added dropwise a solution of 64.7 mg of lithium hydroxide in 8 ml of water under cooling, and the mixture is stirred at room temperature for 1 hour. After the reaction mixture is evaporated under reduced pressure to remove methanol, the residue is dissolved in chloroform. The pH of the solution is adjusted to pH 2 with 10% hydrochloric acid. After extracted with chloroform, the extract is washed with brine twice, dried and evaporated to remove the solvent to give 792 mg of (4S,5R)-3-tert-butoxycarbonyl-2-(4-methoxyphenyl)-4-cyclopropyl-5-oxazolidinecarboxylic acid.

Workup

  1. temperatureunder cooling
  2. customAfter the reaction mixture is evaporated under reduced pressure
  3. customto remove methanol
  4. dissolutionthe residue is dissolved in chloroform
  5. extractionAfter extracted with chloroform
  6. washthe extract is washed with brine twice
  7. customdried
  8. customevaporated
  9. customto remove the solvent

Sources & evidence

ORD record
ord-f4b4bd7ba8a74cfa8166443734cec3e4
Source dataset
uspto-grants-1997_03
Patent number
US05608073

Reaction notes

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