[9-Benzyl-4-carbamoyl-7-methoxy-1,2,3,4-tetrahydrocarbazol-5-yl]oxyacetic acid sodium salt → [9-Benzyl-4-carbamoyl-7-methoxycarbazol-5-yl]oxyacetic acid

HRID 567219Notes

Reaction equation

HRID 567219 reaction equation
[Na+].[CH2:2]([N:9]1[C:21]2[CH2:20][CH2:19][CH2:18][CH:17]([C:22](=[O:24])[NH2:23])[C:16]=2[C:15]2[C:10]1=[CH:11][C:12]([O:30][CH3:31])=[CH:13][C:14]=2[O:25][CH2:26][C:27]([O-:29])=[O:28])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1>[Pd].CCOCCOCCO>[CH2:2]([N:9]1[C:21]2[CH:20]=[CH:19][CH:18]=[C:17]([C:22](=[O:24])[NH2:23])[C:16]=2[C:15]2[C:10]1=[CH:11][C:12]([O:30][CH3:31])=[CH:13][C:14]=2[O:25][CH2:26][C:27]([OH:29])=[O:28])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Participants

4

Reactant 1

HCID 23676539[9-Benzyl-4-carbamoyl-7-methoxy-1,2,3,4-tetrahydrocarbazol-5-yl]oxyacetic acid sodium salt

Product 1

HCID 10135839[9-Benzyl-4-carbamoyl-7-methoxycarbazol-5-yl]oxyacetic acid

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8146Diethylene Glycol Monoethyl EtherSolvent

Procedure

A mixture of 430 mg. of the product from Example 3 Part D, 2.0 gm. of 5% Pd/C, and 20 mL of carbitol was heated to reflux and refluxed for 21 hours, cooled, and filtered. The filtrate was diluted with water, acidified with hydrochloric acid, and extracted well with ethyl acetate. The organic phase was washed with brine, dried over sodium sulfate and evaporated in vacuo. The residue was triturated with dichloromethane and filtered to remove solid tetrahydrocarbazole. The filtrate was evaporated in vacuo to give the title product, 125 mg, 31%.

Workup

  1. additionA mixture of 430 mg
  2. temperatureto reflux
  3. temperaturerefluxed for 21 hours
  4. temperaturecooled
  5. filtrationfiltered
  6. additionThe filtrate was diluted with water
  7. extractionextracted well with ethyl acetate
  8. washThe organic phase was washed with brine
  9. dry with materialdried over sodium sulfate
  10. customevaporated in vacuo
  11. customThe residue was triturated with dichloromethane
  12. filtrationfiltered
  13. customto remove solid tetrahydrocarbazole
  14. customThe filtrate was evaporated in vacuo

Sources & evidence

ORD record
ord-86ba4b2f04984cc59183a9ef552d75ce
Source dataset
uspto-grants-2001_01
Patent number
US06177440B1

Reaction notes

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