Lithium hydroxide, monohydrate → HCID 57151290, compound

HRID 1638178Notes

Reaction equation

HRID 1638178 reaction equation
[C:1]([O:5][C:6]([N:8]1[C@@H:12]([C:13]2[CH:18]=[CH:17][C:16]([I:19])=[CH:15][CH:14]=2)[C@H:11]([C:20]([O:22]C)=[O:21])[O:10][C:9]1([CH3:25])[CH3:24])=[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]2[CH:18]=[CH:17][C:16]([I:19])=[CH:15][CH:14]=2)[C@H:11]([C:20]([OH:22])=[O:21])[O:10][C:9]1([CH3:25])[CH3:24])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 15232285HCID 15232285, compound

Product 1

HCID 57151290HCID 57151290, compoundYield 103.1%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
25 °C

Procedure

To a solution of 1.3 g of methyl (4S,5R)-3-tert-butoxycarbonyl-2,2-dimethyl-4-(4-iodophenyl)-5-oxazolidinecarboxylate in 25 cm3 of ethanol is added, at a temperature in the region of 25° C., a solution of 0.35 g of lithium hydroxide hydrate in 8 cm3 of distilled water. The reaction medium is stirred for 30 minutes at a temperature in the region of 25° C. 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 1N hydrochloric acid solution and extracted with twice 40 cm3 of ethyl acetate. The organic phases are combined, washed with twice 10 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. 1.3 g of (4S,5R)-3-tert-butoxycarbonyl-2,2-dimethyl-4-(4-iodophenyl)-5-oxazolidinecarboxylic acid are thus obtained in the form of a yellow oil.

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 1N hydrochloric acid solution
  6. extractionextracted with twice 40 cm3 of ethyl acetate
  7. washwashed with twice 10 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-07b53910dd9c444eb2649571e1bbe697
Source dataset
uspto-grants-2000_03
Patent number
US06043375

Reaction notes

Loading…