Acetic Acid → HCID 9890404, compound

HRID 2226438Notes

Reaction equation

HRID 2226438 reaction equation
C(O[C:5]([C:7]1[N:8]=[CH:9][C:10]2[N:11](S(C3C=CC(C)=CC=3)(=O)=O)[C:12]3[C:17]([C:18]=2[C:19]=1[CH2:20][O:21][CH3:22])=[CH:16][C:15]([O:23][C:24]1[C:33]2[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=2)[CH:27]=[CH:26][N:25]=1)=[CH:14][CH:13]=3)=[O:6])(C)C.[C:44]1([Li])[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=1.C(O)(=O)C>O1CCCC1.C1C=CC=CC=1>[C:24]1([O:23][C:15]2[CH:16]=[C:17]3[C:12](=[CH:13][CH:14]=2)[NH:11][C:10]2[CH:9]=[N:8][C:7]([C:5](=[O:6])[C:44]4[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=4)=[C:19]([CH2:20][O:21][CH3:22])[C:18]3=2)[C:33]2[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=2)[CH:27]=[CH:26][N:25]=1

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 53649395HCID 53649395, compoundHCID 178506676HCID 178506676, compound

Product 1

HCID 9890404HCID 9890404, compound

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 8028TetrahydrofuranSolvent

Procedure

476 mg of 6-(1-isoquinolyloxy)-4-methoxymethyl-9-tosyl-β-carboline-3-carboxylic acid isopropyl ester is mixed in 10 ml of tetrahydrofuran under argon at -60° C. with 0.79 ml of a 0.9 m solution of phenyllithium in benzene. After 1 hour at -60° C., it is stirred for 16 hours at room temperature. The batch is acidified with glacial acetic acid and concentrated by evaporation. The residue is dispersed in ethyl acetate/water and the organic phase is washed, dried, filtered and concentrated by evaporation in succession with respectively saturated sodium bicarbonate and common salt solution. The residue is chromatographed on silica gel with methylene chloride: ethanol=10:1. The corresponding fractions are combined, concentrated by evaporation and recrystallized. 30 mg of 6-(1-isoquinolyloxy)-4-methoxymethyl-3-benzoyl-β-carboline of melting point 159°-160° C. (ethyl acetate/hexane) is obtained.

Workup

  1. concentrationconcentrated by evaporation
  2. additionThe residue is dispersed in ethyl acetate/water
  3. washthe organic phase is washed
  4. customdried
  5. filtrationfiltered
  6. concentrationconcentrated by evaporation in succession with respectively saturated sodium bicarbonate and common salt solution
  7. customThe residue is chromatographed on silica gel with methylene chloride
  8. concentrationconcentrated by evaporation
  9. customrecrystallized

Sources & evidence

ORD record
ord-ad6082d21c0342f39a321600a133c2d0
Source dataset
uspto-grants-1994_09
Patent number
US05348958

Reaction notes

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