Gramine → 3,3-Dicarboxy-4-(indol-3-yl)butanoic acid

HRID 1741664Notes

Reaction equation

HRID 1741664 reaction equation
CN([CH2:4][C:5]1[C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=2[NH:7][CH:6]=1)C.[CH:14]([C:26]([O:28]CC)=[O:27])([C:21]([O:23]CC)=[O:22])[CH2:15][C:16]([O:18]CC)=[O:17].[Na]>C1(C)C=CC=CC=1>[C:21]([C:14]([C:26]([OH:28])=[O:27])([CH2:4][C:5]1[C:9]2[C:8](=[CH:13][CH:12]=[CH:11][CH:10]=2)[NH:7][CH:6]=1)[CH2:15][C:16]([OH:18])=[O:17])([OH:23])=[O:22]

Participants

5

Reactant 3

HCID 6890GramineHCID 81961Triethyl ethane-1,1,2-tricarboxylateHCID 5360545Sodium

Product 1

HCID 104243533,3-Dicarboxy-4-(indol-3-yl)butanoic acid

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Gramine (17.4 g) and triethyl 1,1,2-ethanetricarboxylate (24.6 g) were suspended in dry toluene. Sodium (0.05 g) was added and the stirred reaction was heated at reflux for six hours. The reaction mixture was cooled, washed with 2N hydrochloric acid (100 ml) and the organic layer was dried (MgSO4) and evaporated. The resulting brown oil was dissolved in ethanol (400 ml) and potassium hydroxide (56 g) was added. The reaction was heated to reflux for six hours, cooled, poured onto ice and acidified to pH1 with 5N hydrochloric acid. The mixture was saturated with sodium sulphate and extracted with ethyl acetate, dried (Na2SO4), filtered and evaporated. The resulting oil was crystallised from 1,2-dichloroethane (400 ml) to yield the title compound, mp 184°-185° C.; found: C, 55.33; H, 4.67; N, 4.32; C14H13NO6. 0.75(H2O) requires C, 55.17; H, 4.80; N, 4.60%.

Workup

  1. customthe stirred reaction
  2. temperaturewas heated
  3. temperatureat reflux for six hours
  4. temperatureThe reaction mixture was cooled
  5. washwashed with 2N hydrochloric acid (100 ml)
  6. dry with materialthe organic layer was dried (MgSO4)
  7. customevaporated
  8. dissolutionThe resulting brown oil was dissolved in ethanol (400 ml)
  9. additionpotassium hydroxide (56 g) was added
  10. temperatureThe reaction was heated
  11. temperatureto reflux for six hours
  12. temperaturecooled
  13. additionpoured onto ice
  14. extractionextracted with ethyl acetate
  15. dry with materialdried (Na2SO4)
  16. filtrationfiltered
  17. customevaporated
  18. customThe resulting oil was crystallised from 1,2-dichloroethane (400 ml)

Sources & evidence

ORD record
ord-24e30f2bc58c453782c7b21f656f7fcd
Source dataset
uspto-grants-1994_08
Patent number
US05334606

Reaction notes

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