HCID 13269012, compound → HCID 54410625, compound

HRID 414202Notes

Reaction equation

HRID 414202 reaction equation
[CH3:1][C:2]1[NH:19][C:18]2[C:20]3[C:3]=1[CH2:4][C@@H:5]1[C:13]([C:14]=3[CH:15]=[CH:16][CH:17]=2)=[CH:12][C@@H:8]([C:9](=[O:11])[OH:10])[CH2:7][N:6]1[CH3:21].Cl.CO.[CH3:25]COCC.CCCCCC>CO>[CH3:25][O:11][C:9]([C@@H:8]1[CH:12]=[C:13]2[C@@H:5]([CH2:4][C:3]3[C:20]4[C:18](=[CH:17][CH:16]=[CH:15][C:14]2=4)[NH:19][C:2]=3[CH3:1])[N:6]([CH3:21])[CH2:7]1)=[O:10]

Participants

5

Reactant 3

HCID 13269012HCID 13269012, compoundHCID 21584099Diethylether hexaneHCID 21893726Hydrochloride methanol

Product 1

HCID 54410625HCID 54410625, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

To a suspension of 25 g 2-methyl-lysergic acid in 500 ml CH3OH are added 253 ml 3.5N HCl/CH3OH. The reaction mixture is then stirred at room temperature for 15 hours, then diluted with 500 ml CH3OH and stirred 2 days. The mixture is evaporated and partitioned between ethyl acetate and 5% K2CO3 solution. After drying and evaporating the heading compound is obtained as crystals, which are then rubbed with ether/hexane (1:1), m.p. 154° (sintering 150°).

Workup

  1. stirringstirred 2 days
  2. customThe mixture is evaporated
  3. custompartitioned between ethyl acetate and 5% K2CO3 solution
  4. customAfter drying
  5. customevaporating the heading compound
  6. customis obtained as crystals, which

Sources & evidence

ORD record
ord-1016a485a19d4a96869fcfd2bbeb3053
Source dataset
uspto-grants-1988_12
Patent number
US04791115

Reaction notes

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