Bicarbonate Ion → HCID 86607069, compound

HRID 2376660Notes

Reaction equation

HRID 2376660 reaction equation
[CH2:1]([O:4][C:5]([NH:7][C:8]1[CH:13]=[C:12]([CH:14]([OH:16])[CH3:15])[CH:11]=[CH:10][C:9]=1[CH2:17][C:18]([O:20][CH2:21][CH3:22])=[O:19])=[O:6])[CH:2]=[CH2:3].C(=O)(O)[O-]>CC(C)=O.[Cl-].[Na+].O>[C:14]([C:12]1[CH:11]=[CH:10][C:9]([CH2:17][C:18]([O:20][CH2:21][CH3:22])=[O:19])=[C:8]([NH:7][C:5]([O:4][CH2:1][CH:2]=[CH2:3])=[O:6])[CH:13]=1)(=[O:16])[CH3:15]

Participants

5

Reactant 2

HCID 769Bicarbonate IonHCID 86607070HCID 86607070, compound

Product 1

HCID 86607069HCID 86607069, compoundYield 100.7%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

Ethyl [2-{[(allyloxy)carbonyl]amino}-4-(1-hydroxyethyl)phenyl]acetate (10.3 g) prepared by step e) was dissolved in acetone (30 mL) and thereto was added at room temperature Jons' reagent (10 mL), followed by stirring for 30 minutes. To the reaction solution were added saturated bicarbonate solution (50 mL) and saturated brine (100 mL), and the mixture was extracted with ethyl acetate (3×50 mL). The organic layer was combined, dried over magnesium sulfate, filtered and the solvent was removed in vacuo to give a crude product. The crude product was combined with the crude product prepared separately prepared in a scale of 1 g and purified with column chromatography (SiO2 300 g, hexane/ethyl acetate 1:1) to give the object compound (10.3 g, 85%) as a yellow oil.

Workup

  1. extractionthe mixture was extracted with ethyl acetate (3×50 mL)
  2. dry with materialdried over magnesium sulfate
  3. filtrationfiltered
  4. customthe solvent was removed in vacuo
  5. customto give a crude product
  6. customprepared separately
  7. customprepared in a scale of 1 g
  8. custompurified with column chromatography (SiO2 300 g, hexane/ethyl acetate 1:1)

Sources & evidence

ORD record
ord-2238cc11b2ec48c1b5b47d23a9ec3c94
Source dataset
uspto-grants-2008_12
Patent number
US07468364B2

Reaction notes

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