Sodium Bicarbonate → HCID 69855343, compound

HRID 987917Notes

Reaction equation

HRID 987917 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH:12]([CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH:11]([CH2:20][CH:21]([CH:31]=O)[CH:22]([C:27]([O:29][CH3:30])=[O:28])[CH2:23][C:24](=[O:26])[CH3:25])[O:10][C:9]1([CH3:34])[CH3:33])=[O:7])([CH3:4])([CH3:3])[CH3:2].O.C1(C)C=CC(S(O)(=O)=O)=CC=1.C(=O)([O-])O.[Na+]>C1(C)C=CC=CC=1>[C:1]([O:5][C:6]([N:8]1[CH:12]([CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH:11]([CH2:20][CH:21]2[CH:22]([C:27]([O:29][CH3:30])=[O:28])[CH2:23][C:24](=[O:26])[CH:25]=[CH:31]2)[O:10][C:9]1([CH3:34])[CH3:33])=[O:7])([CH3:3])([CH3:4])[CH3:2]

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 521998p-Toluenesulfonic acid monohydrateHCID 86759213HCID 86759213, compound

Product 1

HCID 69855343HCID 69855343, compoundYield 45.7%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of 4-benzyl-5-(2-formyl-3-methoxycarbonyl-5-oxo-hexyl)-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester (13.5 g, 27 mmol) and para-toluenesulfonic acid monohydrate (660 mg, 2.7 mmol) in dry toluene (250 ml), was refluxed for 24 hours using a Dean-Stark apparatus to remove water formed during the reaction. The mixture was then cooled to room temperature and treated with and saturated aqueous sodium hydrogen carbonate solution (20 ml). After dilution with ethyl acetate and brine, the layers were separated and the aqueous layer extracted with ethyl acetate. The combined organic layers were washed with brine, dried (anhydrous magnesium sulfate) and concentrated in vacuo. Purification by flash chromatography on silica gel provided 4-benzyl-5-(6-methoxycarbonyl-4-oxo-cyclohex-2-enylmethyl)-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester (5.64 g, 43%). Mass spectrum 458 [M+H]+.

Workup

  1. customto remove water
  2. customformed during the reaction
  3. customAfter dilution with ethyl acetate and brine, the layers were separated
  4. extractionthe aqueous layer extracted with ethyl acetate
  5. washThe combined organic layers were washed with brine
  6. dry with materialdried (anhydrous magnesium sulfate)
  7. concentrationconcentrated in vacuo
  8. customPurification by flash chromatography on silica gel

Sources & evidence

ORD record
ord-0caed817204d47319725e428b1d15f83
Source dataset
uspto-grants-2003_10
Patent number
US06632826B1

Reaction notes

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