Sodium Hydroxide → HCID 86742051, compound

HRID 231705Notes

Reaction equation

HRID 231705 reaction equation
OC(C)(C)[C:3]#[C:4][C:5]1[NH:19][C:18]2[C:20]3[C:6]=1[CH2:7][C@@H:8]1[C:13]([C:14]=3[CH:15]=[CH:16][CH:17]=2)=[CH:12][C@H:11]([NH:21][C:22](=[O:28])[N:23]([CH2:26][CH3:27])[CH2:24][CH3:25])[CH2:10][N:9]1C.[OH-].[Na+]>C1(C)C=CC=CC=1>[C:4]([C:5]1[NH:19][C:18]2[C:20]3[C:6]=1[CH2:7][C@@H:8]1[C:13]([C:14]=3[CH:15]=[CH:16][CH:17]=2)=[CH:12][C@H:11]([NH:21][C:22](=[O:28])[N:23]([CH2:24][CH3:25])[CH2:26][CH3:27])[CH2:10][NH:9]1)#[CH:3]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 70395864HCID 70395864, compound

Product 1

HCID 86742051HCID 86742051, compoundYield 25%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Under nitrogen, 122 mg (0.29 mmol) of 3-[9,10-didehydro-2-(3-hydroxy-3-methyl-1-butynyl)-6-methyl-8α-ergolinyl]-1,1-diethylurea is heated for 2 hours under reflux in 15 ml of absolute toluene after adding 64 mg (1.6 mmol) of pulverized sodium hydroxide. The solvent is then removed by distillation and the residue extracted in ethyl acetate with water and saturated sodium chloride solution. The crude product obtained from the ethyl acetate solution after drying with magnesium sulfate and concentration is purified by column chromatography on 80 g of silica gel with ethyl acetate/ethanol 2:1 as the eluent. Reprecipitation from ethyl acetate/ether/hexane produces 3-(9,10-didehydro-2-ethynyl-8α-ergolinyl)-1,1-diethylurea in a 25% yield.

Workup

  1. customThe solvent is then removed by distillation
  2. extractionthe residue extracted in ethyl acetate with water and saturated sodium chloride solution
  3. customThe crude product obtained from the ethyl acetate solution
  4. dry with materialafter drying with magnesium sulfate and concentration
  5. customis purified by column chromatography on 80 g of silica gel with ethyl acetate/ethanol 2:1 as the eluent
  6. customReprecipitation from ethyl acetate/ether/hexane

Sources & evidence

ORD record
ord-0a06f3af1922432ba68f8f1a7ee9a49a
Source dataset
uspto-grants-1989_07
Patent number
US04847262

Reaction notes

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