HCID 19770980, compound → HCID 19770984, compound

HRID 1589824Notes

Reaction equation

HRID 1589824 reaction equation
C([S:4][CH2:5][CH:6]([CH3:32])[C:7]([N:9]1[CH:21]([C:22]([O:24][CH3:25])=[O:23])[CH2:20][C:19]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[NH:12][C:11]=2[CH:10]1[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)=[O:8])(=O)C>CO>[SH:4][CH2:5][CH:6]([CH3:32])[C:7]([N:9]1[CH:21]([C:22]([O:24][CH3:25])=[O:23])[CH2:20][C:19]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[NH:12][C:11]=2[CH:10]1[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)=[O:8]

Participants

3

Reactant 1

HCID 19770980HCID 19770980, compound

Product 1

HCID 19770984HCID 19770984, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

2-(3'Acetylthio-2'-methylpropanoyl)-1-phenyl-3-carbomethoxy-1,2,3,4-tetrahydro-β-carboline (2 g, 0.045 mole) was dissolved in methanol (75 ml) and anhydrous ammonia was bubbled through the solution for 15 minutes. The reaction was placed under nitrogen and stirring was continued at room temperature for one hour. The methanol was evaporated and the residue was applied to a cation exchange column (methanol). The methanol was evaporated and the residue was dissolved in chloroform, washed with water, dried over magnesium sulfate, filtered and evaporated to give the product as a colorless oil (1.6 g, 88%).

Workup

  1. customanhydrous ammonia was bubbled through the solution for 15 minutes
  2. customThe methanol was evaporated
  3. customThe methanol was evaporated
  4. dissolutionthe residue was dissolved in chloroform
  5. washwashed with water
  6. dry with materialdried over magnesium sulfate
  7. filtrationfiltered
  8. customevaporated

Sources & evidence

ORD record
ord-476268cdfb194fc497c2025294a88230
Source dataset
uspto-grants-1993_04
Patent number
US05200416

Reaction notes

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