Potassium Hydroxide → HCID 18706897, compound

HRID 1422125Notes

Reaction equation

HRID 1422125 reaction equation
[C:1]([NH:4][C:5]1[CH:6]=[CH:7][C:8]2[N:9]3[C:13]=1[C:12]([C:14]([O:16]C)=[O:15])=[CH:11][C:10]3=[C:18]([C:22]1[CH:27]=[CH:26][C:25]([O:28][CH2:29][C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)=[CH:24][CH:23]=1)[C:19]=2[CH2:20][CH3:21])(=[O:3])[CH3:2].[OH-].[K+]>CO>[C:1]([NH:4][C:5]1[CH:6]=[CH:7][C:8]2[N:9]3[C:13]=1[C:12]([C:14]([OH:16])=[O:15])=[CH:11][C:10]3=[C:18]([C:22]1[CH:23]=[CH:24][C:25]([O:28][CH2:29][C:30]3[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=3)=[CH:26][CH:27]=1)[C:19]=2[CH2:20][CH3:21])(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 18707014HCID 18707014, compound

Product 1

HCID 18706897HCID 18706897, compoundYield 94%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of methyl 7-acetylamino-3-(4-benzyloxyphenyl)-4-ethylpyrrolo[2,1,5-cd]indolizine-1-carboxylate (17.15 g, 0.0368 mol) and 85% potassium hydroxide (36.4 g, 0.551 mol) in 1700 ml of methanol was refluxed for 16 hours. The mixture was filtered and the precipitate (shown to be starting material) was further refluxed for 48 hours in 800 ml of methanol and 17.4 g of 85% potassium hydroxide. The mixture was filtered and the filtrate was combined with the first filtrate. The resulting mixture was evaporated to nearly dryness and 1000 ml of water was added. The pH was adjusted to 1.0 with a 6M hydrochloric acid solution. The precipitate was filtered off and dried to afford 15.57 g (94%) of the title compound. M.p. 244-46° C. 1H-NMR (DMSO-d6, 200 MHz) δ: 1.38 (t, 3H), 2.27 (s, 3H), 3.13 (q, 2H), 3.97 (s, 3H), 5.19 (s, 2H), 7.22 (q, 2H), 7.38-7.55 (m, 5H), 7.75 (d, 2H), 7.91 (s, 1H), 8.12 (d, 1H), 8.95 (d, 1H), 11.78 (s, 1H).

Workup

  1. temperaturewas refluxed for 16 hours
  2. filtrationThe mixture was filtered
  3. temperaturethe precipitate (shown to be starting material) was further refluxed for 48 hours in 800 ml of methanol
  4. filtrationThe mixture was filtered
  5. customThe resulting mixture was evaporated to nearly dryness and 1000 ml of water
  6. additionwas added
  7. filtrationThe precipitate was filtered off
  8. customdried

Sources & evidence

ORD record
ord-ba222cff1bb84f87aeff4f18d0847df5
Source dataset
uspto-grants-2000_06
Patent number
US06080754

Reaction notes

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