Lithium Hydroxide → HCID 15549887, compound

HRID 975278Notes

Reaction equation

HRID 975278 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]C)=[O:17])[O:10][C:9]1([CH3:21])[CH3:20])=[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[CH2:14][CH2:15]2)[C@H:11]([C:16]([OH:18])=[O:17])[O:10][C:9]1([CH3:21])[CH3:20])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 15549886HCID 15549886, compound

Product 1

HCID 15549887HCID 15549887, compoundYield 104.5%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a solution of 2.66 g of methyl (4S,5R)-3-tert-butoxycarbonyl-2,2-dimethyl-4-cyclopropyl-5-oxazolidinecarboxylate in 60 ml of methanol is added dropwise a solution of 255 mg of lithium hydroxide in 30 ml of water under ice-cooling. The reaction mixture is warmed to room temperature, stirred for one hour and evaporated under reduced pressure to remove methanol. Chloroform is added to the residue. The pH of the mixture is adjusted to about pH 2 with 10% hydrochloric acid under ice-cooling thereto. The chloroform layer is washed with brine, dried, and evaporated under reduced pressure to remove the solvent to give 2.65 g of (4S,5R)-3-tert-butoxycarbonyl-2,2-dimethyl-4-cyclopropyl-5-oxazolidinecarboxylic acid.

Workup

  1. temperaturecooling
  2. customevaporated under reduced pressure
  3. customto remove methanol
  4. additionChloroform is added to the residue
  5. temperaturecooling
  6. washThe chloroform layer is washed with brine
  7. customdried
  8. customevaporated under reduced pressure
  9. customto remove the solvent

Sources & evidence

ORD record
ord-35df89084327447083629591d1055d19
Source dataset
uspto-grants-1997_03
Patent number
US05608073

Reaction notes

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