Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1) → HCID 71246625, compound

HRID 1620764Notes

Reaction equation

HRID 1620764 reaction equation
[OH:1][C:2]1([C@H:5]2[CH2:9][O:8]C(C)(C)[N:6]2[C:12]([O:14][CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[O:13])[CH2:4][CH2:3]1.CC1C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1.C(=O)([O-])O.[Na+]>CO>[CH2:15]([O:14][C:12](=[O:13])[NH:6][C@@H:5]([C:2]1([OH:1])[CH2:3][CH2:4]1)[CH2:9][OH:8])[C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1

Participants

5

Reactant 3

HCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 516892Sodium BicarbonateHCID 11460510HCID 11460510, compound

Product 1

HCID 71246625HCID 71246625, compoundYield 79.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of benzyl(4R)-4-(1-hydroxycyclopropyl)-2,2-dimethyl-1,3-oxazolidine-3-carboxylate (2.45 g) in methanol (100 mL) was added pyridin-1-ium 4-methylbenzenesulfonate (2.33 g) at room temperature. The reaction mixture was stirred at room temperature overnight, to the reaction mixture was added saturated aqueous sodium hydrogen carbonate solution, and the mixture was extracted with ethyl acetate. The organic layer was separated, washed with saturated brine, dried over magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (1.68 g).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. customThe organic layer was separated
  3. washwashed with saturated brine
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (ethyl acetate/hexane)

Sources & evidence

ORD record
ord-085e1b5cc91a43919c98b6befa203090
Source dataset
uspto-grants-2014_07
Patent number
US08772277B2

Reaction notes

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