Sodium Carbonate → HCID 11681550, compound

HRID 2197653Notes

Reaction equation

HRID 2197653 reaction equation
[C:1]([O:5][C:6]([N:8]1[C@@H:12]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[C@@H:11]([CH:19]=[CH2:20])[O:10][C:9]1([CH3:22])[CH3:21])=[O:7])([CH3:4])([CH3:3])[CH3:2].[OH-:23].[Na+].[OH-:25].[K+].C(=O)([O-])[O-].[Na+].[Na+].C(=O)(O)[O-].[Na+].I([O-])(=O)(=O)=O.[Na+]>[Ru].[Ru](Cl)(Cl)Cl.O.C(Cl)(Cl)(Cl)Cl>[C:1]([O:5][C:6]([N:8]1[C@@H:12]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[C@@H:11]([CH2:19][C:20]([OH:25])=[O:23])[O:10][C:9]1([CH3:22])[CH3:21])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

11

Reactant 6

HCID 10340Sodium CarbonateHCID 14797Potassium HydroxideHCID 14798Sodium HydroxideHCID 516892Sodium BicarbonateHCID 23667635Sodium periodateHCID 68972378HCID 68972378, compound

Product 1

HCID 11681550HCID 11681550, compound

Reagents, catalysts & solvents 4

HCID 23950RutheniumCatalystHCID 61850Ruthenium trichlorideCatalystHCID 962WaterSolventHCID 5943Carbon TetrachlorideSolvent

Conditions

Temperature
12.5 °C

Procedure

(4S,5R)-2,2-Dimethyl-4-phenyl-5-vinyl-oxazolidine-3-carboxylic acid t-butyl ester is dissolved in a polar solvent. Carbon tetrachloride and water are added, followed by the addition of a base such as sodium hydroxide, potassium hydroxide, sodium carbonate, or sodium bicarbonate, at a temperature in the range of about 10-50° C. The reaction mixture is stirred for about 10 to 20 minutes and an alkali metal periodate, such as sodium metaperiodate, is added in small portions to the reaction mixture, such as over a period of about 20 to 40 minutes. A ruthenium salt catalyst, such as ruthenium trichloride, is added to the reaction mixture at a temperature in the range of about 20-40° C. and stirred to reaction completion, such as for about 30-40 hours. The reaction mass is filtered and the filtrate is washed with ethyl acetate, then the aqueous layer is cooled to about 10-15° C. and acidified with 10% aqueous hydrochloric acid to pH 2-3. The aqueous layer is extracted with ethyl acetate, then the organic layer is washed with a 2% aqueous Na2S2O3 solution and washed with brine solution. The organic layer is concentrated at about 50° C. under vacuum to get a thick semi-solid. The solid is triturated with petroleum ether and filtered to get the desired white solid (4S,5R)-5-carboxymethyl-2,2-dimethyl-4-phenyl-oxazolidine-3-carboxylic acid t-butyl ester (I).

Workup

  1. stirringstirred to reaction completion, such as for about 30-40 hours
  2. filtrationThe reaction mass is filtered
  3. washthe filtrate is washed with ethyl acetate
  4. extractionThe aqueous layer is extracted with ethyl acetate
  5. washthe organic layer is washed with a 2% aqueous Na2S2O3 solution
  6. washwashed with brine solution
  7. concentrationThe organic layer is concentrated at about 50° C. under vacuum
  8. customto get a thick semi-solid
  9. customThe solid is triturated with petroleum ether
  10. filtrationfiltered

Sources & evidence

ORD record
ord-62c0bfcff48545caaa5e1d62fc713806
Source dataset
uspto-grants-2012_12
Patent number
US08338617B2

Reaction notes

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