1,4-Dioxane → 5,6,7,13-Tetrahydro-5-oxo-12H-indolo[2,3-a]pyrrolo[3,4-c]carbazole-12-propanoic acid

HRID 2395708Notes

Reaction equation

HRID 2395708 reaction equation
C([O:5][C:6]([CH2:8][CH2:9][N:10]1[C:22]2[C:21]3[NH:23][C:24]4[CH:25]=[CH:26][CH:27]=[CH:28][C:29]=4[C:20]=3[C:19]3[C:30](=[O:33])[NH:31][CH2:32][C:18]=3[C:17]=2[C:16]2[C:11]1=[CH:12][CH:13]=[CH:14][CH:15]=2)=[O:7])(C)(C)C.O1CCOCC1>Cl>[C:6]([CH2:8][CH2:9][N:10]1[C:22]2[C:21]3[NH:23][C:24]4[CH:25]=[CH:26][CH:27]=[CH:28][C:29]=4[C:20]=3[C:19]3[C:30](=[O:33])[NH:31][CH2:32][C:18]=3[C:17]=2[C:16]2[C:11]1=[CH:12][CH:13]=[CH:14][CH:15]=2)([OH:7])=[O:5]

Participants

4

Reactant 2

HCID 312751,4-DioxaneHCID 18989885HCID 18989885, compound

Product 1

HCID 189898865,6,7,13-Tetrahydro-5-oxo-12H-indolo[2,3-a]pyrrolo[3,4-c]carbazole-12-propanoic acid

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

147 mg (0.33 mmole) 12-(2-tert.-butoxycarbonylethyl)-6,7,12,13-tetrahydro-5-oxo-5H-indolo[2,3-a]pyrrolo[3,4-c]carbazole are stirred for 16 hours at 20° C. in 5 mL 18% hydrochloric acid and 5 mL dioxan and then for 2 hours at 50° C. The product formed is filtered off, washed with a little water and ethanol and dried in a vacuum at 90° C. 12-(2-Carboxyethyl)-6,7,12,13-tetrahydro-5-oxo-5H-indolo[2,3-a]pyrrolo[3,4-c]carbazole is obtained in the form of pale beige crystals which decompose above 320° C.

Workup

  1. customThe product formed
  2. filtrationis filtered off
  3. washwashed with a little water and ethanol
  4. customdried in a vacuum at 90° C

Sources & evidence

ORD record
ord-9fcd302fc8f34e27a1175d759c147b68
Source dataset
uspto-grants-1996_02
Patent number
US05489608

Reaction notes

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