HCID 131715472, compound → HCID 131715474, compound

HRID 231717Notes

Reaction equation

HRID 231717 reaction equation
[Si]([N:8]1[C:22]2[C:23]3[C:10]([CH2:11][C@@H:12]4[C:17]([C:18]=3[CH:19]=[CH:20][CH:21]=2)=[CH:16][C@H:15]([NH:24][C:25](=[O:31])[N:26]([CH2:29][CH3:30])[CH2:27][CH3:28])[CH2:14][N:13]4[CH3:32])=[C:9]1[CH3:33])(C(C)(C)C)(C)C>CO.O1CCCC1.[Cl-].[Na+]>[CH3:33][C:9]1[NH:8][C:22]2[C:23]3[C:10]=1[CH2:11][C@@H:12]1[C:17]([C:18]=3[CH:19]=[CH:20][CH:21]=2)=[CH:16][C@H:15]([NH:24][C:25](=[O:31])[N:26]([CH2:29][CH3:30])[CH2:27][CH3:28])[CH2:14][N:13]1[CH3:32]

Participants

5

Reactant 1

HCID 131715472HCID 131715472, compound

Product 1

HCID 131715474HCID 131715474, compoundYield 68.4%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 5234Sodium ChlorideSolventHCID 8028TetrahydrofuranSolvent

Procedure

Under argon, 183 mg (0.39 mmol) of 3-[1-(tert-butyldimethylsilyl)-9,10-didehydro-2,6-dimethyl-8α-ergolinyl]-1,1-diethylurea is dissolved in 5 ml of methanol with addition of 2 ml of tetrahydrofuran and stirred with 1 ml of 14N potassium hydroxide solution at room temperature for 17 hours. To work up the mixture, it is diluted with saturated sodium chloride solution and extracted with methylene chloride. The methylene chloride extracts are washed with saturated sodium chloride solution and water and dried over sodium sulfate. The crude product of 128 mg is chromatographed and crystallized as the tartrate, thus obtaining 94 mg (67% of theory) of 3-(9,10-didehydro-2,6-dimethyl-8α-ergolinyl)-1,1-diethylurea.

Workup

  1. extractionextracted with methylene chloride
  2. washThe methylene chloride extracts are washed with saturated sodium chloride solution and water
  3. dry with materialdried over sodium sulfate
  4. customThe crude product of 128 mg is chromatographed
  5. customcrystallized as the tartrate

Sources & evidence

ORD record
ord-7397897b328a422d933850b4f8691c69
Source dataset
uspto-grants-1989_07
Patent number
US04847262

Reaction notes

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