Sodium Hydroxide → HCID 57268046, compound

HRID 365348Notes

Reaction equation

HRID 365348 reaction equation
[OH-].[Na+].[CH:3]([O:6][C:7]([C:9]1[N:10]=[CH:11][C:12]2[NH:13][C:14]3[C:19]([C:20]=2[C:21]=1[CH2:22][CH3:23])=[CH:18][C:17]([NH:24][C:25](=[S:27])[CH3:26])=[CH:16][CH:15]=3)=[O:8])([CH3:5])[CH3:4]>O.N1C=CC=CC=1.C(OCC)(=O)C>[CH:3]([O:6][C:7]([C:9]1[N:10]=[CH:11][C:12]2[NH:13][C:14]3[C:19]([C:20]=2[C:21]=1[CH2:22][CH3:23])=[C:18]1[S:27][C:25]([CH3:26])=[N:24][C:17]1=[CH:16][CH:15]=3)=[O:8])([CH3:5])[CH3:4]

Participants

6

Reactant 2

HCID 14798Sodium HydroxideHCID 53883802HCID 53883802, compound

Product 1

HCID 57268046HCID 57268046, compoundYield 15.1%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 1049PyridineSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
4 °C

Procedure

450 mg of K3Fe(CN)6 is dissolved in 1.8 ml of water, mixed with 1.4 ml of 1N NaOH and cooled to 4° C. 200 mg of 4-ethyl-6-thioacetylamino-β-carboline-3-carboxylic acid isopropyl ester in 4 ml of pyridine is added in drops to this solution and stirred for another 2 hours at this temperature. The reaction mixture is taken up in ethyl acetate, washed with water, dried and concentrated by evaporation. The residue is chromatographed on silica gel with toluene+ethanol=95+5. The desired fractions are concentrated by evaporation and stirred up with ether. 30 mg of the title compound with a melting point of 239-240° C. is obtained.

Workup

  1. washwashed with water
  2. customdried
  3. concentrationconcentrated by evaporation
  4. customThe residue is chromatographed on silica gel with toluene+ethanol=95+5
  5. concentrationThe desired fractions are concentrated by evaporation
  6. stirringstirred up with ether

Sources & evidence

ORD record
ord-0d8760b0e1f34d91958b7f6941cb1d53
Source dataset
uspto-grants-2000_10
Patent number
US06127368

Reaction notes

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