Acetone → {[2-(7-Methoxy-benzo[1,3]dioxole-5-carbonyl)-benzenesulfonyl]-o-tolyl-amino}-acetic acid methyl ester

HRID 1069485

Reaction equation

HRID 1069485 reaction equation
CC(C)=O.[CH3:5][O:6][C:7](=[O:39])[CH2:8][N:9]([S:17]([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=1[CH:26]([OH:38])[C:27]1[CH:35]=[C:34]([O:36][CH3:37])[C:30]2[O:31][CH2:32][O:33][C:29]=2[CH:28]=1)(=[O:19])=[O:18])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[CH3:16].CC(C)=O.OS(O)(=O)=O.O=[Cr](=O)=O.C(O)(C)C>C(OCC)(=O)C>[CH3:5][O:6][C:7](=[O:39])[CH2:8][N:9]([S:17]([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=1[C:26]([C:27]1[CH:35]=[C:34]([O:36][CH3:37])[C:30]2[O:31][CH2:32][O:33][C:29]=2[CH:28]=1)=[O:38])(=[O:18])=[O:19])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[CH3:16]

Participants

6

Reactant 4

HCID 180AcetoneHCID 3776IsopropanolHCID 22965597({2-[Hydroxy-(7-methoxy-benzo[1,3]dioxol-5-yl)-methyl]-benzenesulfonyl}-o-tolyl-amino)-acetic acid methyl esterHCID 131709961Jones' reagent

Product 1

HCID 22965596{[2-(7-Methoxy-benzo[1,3]dioxole-5-carbonyl)-benzenesulfonyl]-o-tolyl-amino}-acetic acid methyl esterYield 59%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To acetone (225 mL) was added ({2-[hydroxy-(7-methoxy-benzo[1,3]dioxol-5-yl)-methyl]-benzenesulfonyl}-o-tolyl-amino)-acetic acid methyl ester (4.17 g, 8.35 mmol), and 8N Jones reagent (4 mL). The mixture was stirred 15 minutes giving a suspended solid. Isopropanol (20 mL) was added followed by stirring for 15 minutes. The mixture was filtered, saturated sodium bicarbonate solution was added, and the solvent was removed in vacuo giving a paste. The paste was resuspended in ethyl acetate and water, filtered, and washed with saturated sodium bicarbonate, brine and dried over anhydrous magnesium sulfate. The solution was filtered and evaporated to a solid which was crystallized from ethyl acetate and ethyl ether giving a white solid, 2.41 g, 59% yield, mp 159-170° C. NMR spectra and elemental analysis were consistent with the structure.

Workup

  1. customgiving a suspended solid
  2. stirringby stirring for 15 minutes
  3. filtrationThe mixture was filtered
  4. additionsaturated sodium bicarbonate solution was added
  5. customthe solvent was removed in vacuo
  6. customgiving a paste
  7. filtrationwater, filtered
  8. washwashed with saturated sodium bicarbonate, brine
  9. dry with materialdried over anhydrous magnesium sulfate
  10. filtrationThe solution was filtered
  11. customevaporated to a solid which
  12. customwas crystallized from ethyl acetate and ethyl ether giving a white solid, 2.41 g, 59% yield, mp 159-170° C

Sources & evidence

ORD record
ord-8359ecf4f77845398f2050a98f4449de
Source dataset
uspto-grants-2001_06
Patent number
US06252070B1

Linked notes

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