Lithium hydroxide, monohydrate → HCID 57298287, compound

HRID 1638181Notes

Reaction equation

HRID 1638181 reaction equation
[C:1]([O:5][C:6]([N:8]1[C@H:12]([C:13]([O:15][CH:16]([CH3:25])[C:17]2[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[CH:19][CH:18]=2)=[O:14])[C@H:11]([C:26]([O:28]C)=[O:27])[O:10][C:9]1([CH3:31])[CH3:30])=[O:7])([CH3:4])([CH3:3])[CH3:2].O.[OH-].[Li+]>C(O)C.O>[C:1]([O:5][C:6]([N:8]1[C@H:12]([C:13]([O:15][CH:16]([CH3:25])[C:17]2[CH:18]=[CH:19][C:20]([O:23][CH3:24])=[CH:21][CH:22]=2)=[O:14])[C@H:11]([C:26]([OH:28])=[O:27])[O:10][C:9]1([CH3:30])[CH3:31])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 57082188HCID 57082188, compound

Product 1

HCID 57298287HCID 57298287, compoundYield 93.5%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

To a solution of 2.1 g of methyl (4S,5R)-3-tert-butoxycarbonyl-2,2-dimethyl-4-[α-methyl-(4-methoxy)benzyloxycarbonyl]-5-oxazolidinecarboxylate in 55 cm3 of ethanol is added, at a temperature in the region of 25° C., a solution of 0.172 g of lithium hydroxide hydrate in 10 cm3 of distilled water. The reaction medium is stirred for 2 hours at a temperature in the region of 20° and then concentrated to dryness under reduced pressure (2.7 kPa) at a temperature in the region of 40° C. The evaporation residue is dissolved in 20 cm3 of distilled water and the solution obtained is washed with twice 15 cm3 of diethyl ether, acidified to a pH in the region of 2 by addition of aqueous 0.5N hydrochloric acid solution and extracted with twice 100 cm3 of ethyl acetate. The organic phases are combined, washed with twice 15 cm3 of distilled water, dried over magnesium sulphate, filtered and then concentrated to dryness under reduced pressure (2.7 kPa) at a temperature in the region of 40° C. 1.9 g of (4S,5R)-3-tert-butoxycarbonyl-2,2-dimethyl-4-[α-methyl-(4-methoxy)benzyloxycarbonyl]-5-oxazolidinecarboxylic acid are thus obtained in the form of a white foam.

Workup

  1. concentrationconcentrated to dryness under reduced pressure (2.7 kPa) at a temperature in the region of 40° C
  2. dissolutionThe evaporation residue is dissolved in 20 cm3 of distilled water
  3. customthe solution obtained
  4. washis washed with twice 15 cm3 of diethyl ether
  5. additionacidified to a pH in the region of 2 by addition of aqueous 0.5N hydrochloric acid solution
  6. extractionextracted with twice 100 cm3 of ethyl acetate
  7. washwashed with twice 15 cm3 of distilled water
  8. dry with materialdried over magnesium sulphate
  9. filtrationfiltered
  10. concentrationconcentrated to dryness under reduced pressure (2.7 kPa) at a temperature in the region of 40° C

Sources & evidence

ORD record
ord-f65f9a81fad9418c961f72198211e9ac
Source dataset
uspto-grants-2000_03
Patent number
US06043375

Reaction notes

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