Acetic Acid → HCID 11212836, compound

HRID 988311Notes

Reaction equation

HRID 988311 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[CH2:23][CH2:22][C:21]2[C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[NH:14][C:13]=2[CH:12]1[C:24]1[CH:29]=[CH:28][C:27]2[O:30][CH2:31][O:32][C:26]=2[CH:25]=1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CC(C)([O-:36])C.[K+].O=O.C(O)(=O)C>CN(C=O)C.O>[CH2:1]([O:8][C:9]([N:11]1[CH2:23][C:22]2[C:21](=[O:36])[C:20]3[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=3[NH:14][C:13]=2[CH:12]1[C:24]1[CH:29]=[CH:28][C:27]2[O:30][CH2:31][O:32][C:26]=2[CH:25]=1)=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 977OxygenHCID 10274041HCID 10274041, compoundHCID 23665647Potassium tert-butoxide

Product 1

HCID 11212836HCID 11212836, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

2-benzyloxycarbonyl-1-(3,4-methylenedioxyphenyl)-2,3,4,9-tetrahydro-1H-β-carboline (3.63 g, 8.51 mmol) ) (prepared as in Example 10) was dissolved in dry DMF (25 mL). Potassium t-butoxide (2.40 g, 21.4 mmol) was introduced in one portion and the suspension was stirred until a clear solution was obtained. Oxygen gas was then passed through the solution via a syringe needle for 16 h. The reaction was quenched by the addition of glacial acetic acid (1.23 mL, 21.0 mmol) and poured into water (250 mL), which resulted in a precipitate that was collected by filtration. The product was purified by flash chromatography (2-10% MeOH/CHCl3) to yield the product as a red powder.

Workup

  1. customwas obtained
  2. customresulted in a precipitate that
  3. filtrationwas collected by filtration
  4. customThe product was purified by flash chromatography (2-10% MeOH/CHCl3)

Sources & evidence

ORD record
ord-4c61c50ce7484d32b7b8f055e9c185a1
Source dataset
uspto-grants-2003_10
Patent number
US06635638B2

Reaction notes

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