Sodium Bicarbonate → HCID 86749311, compound

HRID 1439952Notes

Reaction equation

HRID 1439952 reaction equation
[CH3:1][O:2][C:3]([C:5]1[C:13]2[O:12][CH:11]3[CH2:14][CH:15]([OH:20])[CH:16]([N:17]=[N+:18]=[N-:19])[CH:10]3[C:9]=2[CH:8]=[CH:7][CH:6]=1)=[O:4].[C:21](=[O:24])([O-])O.[Na+]>C1COCC1.C1(C)C=CC(S(O)(=O)=O)=CC=1.O1C=CCCC1>[CH3:1][O:2][C:3]([C:5]1[C:13]2[O:12][CH:11]3[CH2:14][CH:15]([O:20][CH:7]4[CH2:6][CH2:5][CH2:3][CH2:21][O:24]4)[CH:16]([N:17]=[N+:18]=[N-:19])[CH:10]3[C:9]=2[CH:8]=[CH:7][CH:6]=1)=[O:4]

Participants

6

Reactant 2

HCID 516892Sodium BicarbonateHCID 86749312HCID 86749312, compound

Product 1

HCID 86749311HCID 86749311, compound

Reagents, catalysts & solvents 3

HCID 6101p-Toluenesulfonic acidSolventHCID 8028TetrahydrofuranSolventHCID 80803,4-dihydro-2H-pyranSolvent

Procedure

(1RS, 2RS, 3aSR, 8bRS)-1-azido-2-hydroxy-2,3,3a,8b-tetrahydro-1H-cyclopenta[b]benzofuran-5-carboxylic acid methyl ester (2) (2.5 g) was dissolved in anhydrous THF (40 ml) followed-by addition of a catalytic amount of p-toluenesulfonic acid and 2,3-dihydropyrane (1.64 ml) and stirring for 16 hours at room temperature. A saturated aqueous solution of sodium hydrogencarbonate (50 ml) was added to the reaction mixture followed by extraction with ethyl acetate (150 ml, 100 ml), combining of the organic layers, washing with water (50 ml) and saturated brine (50 ml) and concentration after drying with magnesium sulfate. The resulting residue was purified with column chromatography (silica gel: ethyl acetate/cyclohexane 1/10) to obtain the target confound (3.2 g, 98%).

Workup

  1. extractionfollowed by extraction with ethyl acetate (150 ml, 100 ml)
  2. washwashing with water (50 ml) and saturated brine (50 ml) and concentration
  3. dry with materialafter drying with magnesium sulfate
  4. customThe resulting residue was purified with column chromatography (silica gel: ethyl acetate/cyclohexane 1/10)
  5. customto obtain the target confound (3.2 g, 98%)

Sources & evidence

ORD record
ord-f66c3503df6b456795d2cadd71d6e35d
Source dataset
uspto-grants-1996_03
Patent number
US05496849

Reaction notes

Loading…