Lithium Hydroxide → HCID 15276496, compound

HRID 1489454Notes

Reaction equation

HRID 1489454 reaction equation
[OH-].[Li+].[C:3]([O:7][C:8]([N:10]1[C@@H:14]([C:15]2[CH:20]=[CH:19][C:18]([F:21])=[CH:17][C:16]=2[F:22])[C@H:13]([C:23]([O:25]C)=[O:24])[O:12][C:11]1([CH3:28])[CH3:27])=[O:9])([CH3:6])([CH3:5])[CH3:4]>O.CO>[C:3]([O:7][C:8]([N:10]1[C@@H:14]([C:15]2[CH:20]=[CH:19][C:18]([F:21])=[CH:17][C:16]=2[F:22])[C@H:13]([C:23]([OH:25])=[O:24])[O:12][C:11]1([CH3:28])[CH3:27])=[O:9])([CH3:6])([CH3:4])[CH3:5]

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 15276490HCID 15276490, compound

Product 1

HCID 15276496HCID 15276496, compoundYield 99.5%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

Under ice cooling, a solution of 31 mg of lithium hydroxide dissolved in 5 ml of water was added dropwise to a solution of 402 mg of methyl (4S,5R)-3-tert-butoxycarbonyl-2,2-dimethyl-4-(2,4-difluorophenyl)-5-oxazolidinecarboxylate dissolved in 10 ml of methanol. After the mixture was stirred at room temperature for 45 minutes, the reaction mixture was concentrated under reduced pressure. Water and diethyl ether were added to the residue, and the aqueous layer was collected by separation. The aqueous layer was adjusted to about pH 2 by adding 10% aqueous hydrochloric acid thereto under ice cooling and then extracted with chloroform. After the chloroform layer was washed with water and dried, the solvent was removed to obtain 385 mg of (4S,5R)-3-tert-butoxycarbonyl-2,2-dimethyl-4-(2,4-difluorophenyl)-5-oxazolidinecarboxylic acid.

Workup

  1. concentrationthe reaction mixture was concentrated under reduced pressure
  2. additionWater and diethyl ether were added to the residue
  3. customthe aqueous layer was collected by separation
  4. additionby adding 10% aqueous hydrochloric acid
  5. extractionunder ice cooling and then extracted with chloroform
  6. washAfter the chloroform layer was washed with water
  7. customdried
  8. customthe solvent was removed

Sources & evidence

ORD record
ord-216a392be130480799c100a3215047ce
Source dataset
uspto-grants-1997_10
Patent number
US05677470

Reaction notes

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