Ethyl Acetate → HCID 53883802, compound

HRID 365347Notes

Reaction equation

HRID 365347 reaction equation
[CH:1]([O:4][C:5]([C:7]1[N:8]=[CH:9][C:10]2[NH:11][C:12]3[C:17]([C:18]=2[C:19]=1[CH2:20][CH3:21])=[CH:16][C:15]([NH:22][C:23](=O)[CH3:24])=[CH:14][CH:13]=3)=[O:6])([CH3:3])[CH3:2].COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:35])=CC=1.C(OCC)(=O)C>O1CCOCC1>[CH:1]([O:4][C:5]([C:7]1[N:8]=[CH:9][C:10]2[NH:11][C:12]3[C:17]([C:18]=2[C:19]=1[CH2:20][CH3:21])=[CH:16][C:15]([NH:22][C:23](=[S:35])[CH3:24])=[CH:14][CH:13]=3)=[O:6])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 87949Lawesson's reagentHCID 54114684HCID 54114684, compound

Product 1

HCID 53883802HCID 53883802, compoundYield 53.7%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

2741 mg of 6-acetylamino-4-ethyl-β-carboline-3-carboxylic acid isopropyl ester is heated to 70° C. in 110 ml of dioxane with 3915 mg of Lawesson's reagent while being stirred. After cooling, it is mixed with 100 ml of ethyl acetate and washed with saturated sodium chloride solution. The organic phases are dried and concentrated by evaporation in a vacuum. The residue is chromatographed on silica gel with toluene+methanol=8+2. 1541 mg of 4-ethyl-6-thioacetylamino-β-carboline-3-carboxylic acid isopropyl ester with a melting point of 158-160° C. is obtained from the desired fractions.

Workup

  1. temperatureAfter cooling
  2. washwashed with saturated sodium chloride solution
  3. customThe organic phases are dried
  4. concentrationconcentrated by evaporation in a vacuum
  5. customThe residue is chromatographed on silica gel with toluene+methanol=8+2

Sources & evidence

ORD record
ord-13b3ea3ebcb8487696dff6f1cce816f1
Source dataset
uspto-grants-2000_10
Patent number
US06127368

Reaction notes

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