Lithium hydroxide, monohydrate → (4S,5R)-3-(tert-Butoxycarbonyl)-2,2-dimethyl-4-phenyl-1,3-oxazolidine-5-carboxylic acid

HRID 2260388Notes

Reaction equation

HRID 2260388 reaction equation
O.[OH-].[Li+].[C:4]([O:8][C:9]([N:11]1[C@@H:15]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[C@H:14]([C:22]([O:24]CC)=[O:23])[O:13][C:12]1([CH3:28])[CH3:27])=[O:10])([CH3:7])([CH3:6])[CH3:5]>O.C(O)C>[C:4]([O:8][C:9]([N:11]1[C@@H:15]([C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=2)[C@H:14]([C:22]([OH:24])=[O:23])[O:13][C:12]1([CH3:28])[CH3:27])=[O:10])([CH3:7])([CH3:5])[CH3:6]

Participants

5

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 299746193-tert-Butyl 5-ethyl (4S,5R)-2,2-dimethyl-4-phenyl-1,3-oxazolidine-3,5-dicarboxylate

Product 1

HCID 10969286(4S,5R)-3-(tert-Butoxycarbonyl)-2,2-dimethyl-4-phenyl-1,3-oxazolidine-5-carboxylic acidYield 96%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent2×

Procedure

A solution of 4.62 g of lithium hydroxide hydrate in 80 cm3 of water is added in the course of 10 minutes to a stirred solution of 12.8 g of ethyl (4S,5R)-3-tert-butoxycarbonyl-2,2-dimethyl-4-phenyl-5-oxazolidinecarboxylate in 200 cm3 of ethanol. After stirring for a further 10 minutes, the reaction medium is concentrated to dryness under reduced pressure (2.7kPa) at a temperature in the region of 40° C. The residue obtained is dissolved in 70 cm3 of water and then extracted with 3 times 20 cm3 of isopropyl ether. The aqueous phase is then acidified to a pH in the region of 2.6 by adding approximately 100 cc of 1N aqueous hydrochloric acid solution and thereafter extracting with 3 times 50 cm3 of dichloromethane. The combined organic phases are 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. 11.3 g of (4S,5R)-3-tert-butoxycarbonyl-2,2-dimethyl-4-phenyl-5-oxazolidinecarboxylic acid are thereby obtained in the form of a yellow oil, the characteristics of which are as follows:

Workup

  1. concentrationthe reaction medium is concentrated to dryness under reduced pressure (2.7kPa) at a temperature in the region of 40° C
  2. customThe residue obtained
  3. extractionextracted with 3 times 20 cm3 of isopropyl ether
  4. additionby adding approximately 100 cc of 1N aqueous hydrochloric acid solution
  5. extractionextracting with 3 times 50 cm3 of dichloromethane
  6. dry with materialThe combined organic phases are dried over magnesium sulphate
  7. filtrationfiltered
  8. concentrationconcentrated to dryness under reduced pressure (2.7 kPa) at a temperature in the region of 40° C

Sources & evidence

ORD record
ord-356098d54993488e923b26e922caba55
Source dataset
uspto-grants-1995_12
Patent number
US05476954

Reaction notes

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