Dimethylformamide → 1-(1-Ethylpropyl)-6-methylergoline-8carboxylic acid

HRID 570040Notes

Reaction equation

HRID 570040 reaction equation
[CH3:1][N:2]1[CH:7]2[CH2:8][C:9]3[C:17]4[C:12](=[CH:13][CH:14]=[CH:15][C:16]=4[CH:6]2[CH2:5][CH:4]([C:18]([OH:20])=[O:19])[CH2:3]1)[NH:11][CH:10]=3.[OH-].[K+].CN(C=O)C.[C:28]1(C)[CH:33]=[CH:32]C(S(OC(CC)CC)(=O)=O)=[CH:30][CH:29]=1>O>[CH2:29]([CH:28]([N:11]1[C:12]2[C:17]3[C:9]([CH2:8][C@@H:7]4[C@@H:6]([C:16]=3[CH:15]=[CH:14][CH:13]=2)[CH2:5][CH:4]([C:18]([OH:20])=[O:19])[CH2:3][N:2]4[CH3:1])=[CH:10]1)[CH2:33][CH3:32])[CH3:30]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 14797Potassium HydroxideHCID 622987NoName_3979HCID 12568537Pentan-3-yl 4-methylbenzene-1-sulfonate

Product 1

HCID 138780051-(1-Ethylpropyl)-6-methylergoline-8carboxylic acidYield 57%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a 50 ml, three-neck round bottom flask was added 1.0 g (3.4 mmol) of 92% pure 9,10-dihydrolysergic acid, 1.03 g (15.8 mmol) of 86% pure powdered potassium hydroxide and 15 ml of DMF. This mixture was agitated until the solids were dissolved, and 1.79 g (7.4 mmol) of p-toluenesulfonic acid, 1-ethylpropyl ester was added. The reaction mixture was stirred for 19 hours at room temperature, and 35 ml of water was added. The reaction mixture was washed into a 250 ml erlenmeyer flask with deionized water, and the mixture was washed with 50 ml of methylene chloride. The aqueous layer was separated, saturated with an aqueous sodium chloride solution and washed with methylene chloride. The emulsified aqueous layer and the second organic layer were combined and the pH was adjusted to 6. The organic layer was separated and filtered by vacuum filtration. The resulting solid was washed with methylene chloride and dried in vacuo to provide 0.66 g of the title compound. The purity of the solid was 96.8% as determined by high performance liquid chromatography (HPLC). mp =187° -189° C. Exact mass: theory 341.22290; found 341.22261.

Workup

  1. dissolutionwere dissolved
  2. stirringThe reaction mixture was stirred for 19 hours at room temperature
  3. washThe reaction mixture was washed into a 250 ml erlenmeyer flask with deionized water
  4. washthe mixture was washed with 50 ml of methylene chloride
  5. customThe aqueous layer was separated, saturated with an aqueous sodium chloride solution
  6. washwashed with methylene chloride
  7. customThe organic layer was separated
  8. filtrationfiltered by vacuum filtration
  9. washThe resulting solid was washed with methylene chloride
  10. customdried in vacuo

Sources & evidence

ORD record
ord-1ae836427102440ba3f8a65a65eae598
Source dataset
uspto-grants-1988_03
Patent number
US04734501

Reaction notes

Loading…