Sodium Bicarbonate → 2-(4-Nitrophenyl)ethyl 3-(pyrrolo[4,5-e]indolin-7-ylcarbonyl)pyrrolo[4,5-e]indoline-7-carboxylate

HRID 599377Notes

Reaction equation

HRID 599377 reaction equation
C(OC([N:8]1[C:19]2[C:11](=[C:12]3[C:16](=[CH:17][CH:18]=2)[NH:15][CH:14]([C:20]([N:22]2[C:33]4[C:25](=[C:26]5[C:30](=[CH:31][CH:32]=4)[NH:29][CH:28]([C:34]([O:36][CH2:37][CH2:38][C:39]4[CH:44]=[CH:43][C:42]([N+:45]([O-:47])=[O:46])=[CH:41][CH:40]=4)=[O:35])[CH2:27]5)[CH:24]=[CH:23]2)=[O:21])[CH2:13]3)[CH:10]=[CH:9]1)=O)(C)(C)C.C(=O)(O)[O-].[Na+]>FC(F)(F)C(O)=O>[CH:10]1[C:11]2=[C:12]3[C:16](=[CH:17][CH:18]=[C:19]2[NH:8][CH:9]=1)[NH:15][CH:14]([C:20]([N:22]1[C:33]2[C:25](=[C:26]4[C:30](=[CH:31][CH:32]=2)[NH:29][CH:28]([C:34]([O:36][CH2:37][CH2:38][C:39]2[CH:40]=[CH:41][C:42]([N+:45]([O-:47])=[O:46])=[CH:43][CH:44]=2)=[O:35])[CH2:27]4)[CH:24]=[CH:23]1)=[O:21])[CH2:13]3

Participants

4

Reactant 2

HCID 516892Sodium BicarbonateHCID 667169682-(4-Nitrophenyl)ethyl 3-({3-[(tert-butyl)oxycarbonyl]pyrrolo[4,5-e]indolin-7-yl}carbonyl)pyrrolo[4,5-e]indoline-7-carboxylate

Product 1

HCID 667169662-(4-Nitrophenyl)ethyl 3-(pyrrolo[4,5-e]indolin-7-ylcarbonyl)pyrrolo[4,5-e]indoline-7-carboxylate

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

5 grams of 16 are placed in a flask. 100 mL of trifluoroacetic acid is added, and the mixture is stirred. After an hour, the acid is evaporated on a rotary evaporator and 100 mL saturated sodium bicarbonate solution and 100 mL of water are added. The mixture is agitated or sonicated for ˜½ hours, then filtered and washed with water and then methanol, and dried in vacuo. The material may be recrystallized. It is dissolved in a minimum amount of warm DMF, and then approximately a threefold portion of methanol is added and the solution is sonicated a few minutes. A cream to brown material crystallizes out. This is washed with methanol, and dried in vacua The yield approaches theoretical values. 1H NMR (DMSO-d6) δ 11.96 (s, NH, 1H), 11.71 (s, NH, 1H), 8.30 (br s, aromatic proton, 1H), 8.27 (br s, aromatic proton, 1H), 8.19 (d, aromatic protons, J=8.5 Hz, 2H), 7.66 (d, aromatic protons, J=8.3 Hz, 2H), 7.34 (m, aromatic protons, 2H), 7.08 (s, aromatic proton, 1H), 7.03 (s, aromatic proton, 1H), 4.60 (m, aliphatic protons, 4H), 3.68 (t, J=8 Hz, aliphatic protons, 2H), 3.40 (t, J=8 Hz, aliphatic protons, 2H), 3.24 (m, aliphatic protons, 4H). Combustion Analysis: Found: C, 63.55%; H, 4.42%; N, 11.95%. Calculated, for ½ mole sodium bicarbonate contaminant: C, 63.43%; H, 4.45%; N, 12.13%.

Workup

  1. waitAfter an hour
  2. customthe acid is evaporated on a rotary evaporator and 100 mL saturated sodium bicarbonate solution and 100 mL of water
  3. additionare added
  4. stirringThe mixture is agitated
  5. customsonicated for ˜½ hours
  6. filtrationfiltered
  7. washwashed with water
  8. dry with materialmethanol, and dried in vacuo
  9. customThe material may be recrystallized
  10. dissolutionIt is dissolved in a minimum amount of warm DMF
  11. additionapproximately a threefold portion of methanol is added
  12. customthe solution is sonicated a few minutes
  13. customA cream to brown material crystallizes out
  14. washThis is washed with methanol
  15. customdried in vacua The yield

Sources & evidence

ORD record
ord-40316a2d2c7f4cff8dace857a2ac92cd
Source dataset
uspto-grants-2011_03
Patent number
US07897736B2

Reaction notes

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