1413-67-8 → HCID 21156211, compound

HRID 1905369Notes

Reaction equation

HRID 1905369 reaction equation
[OH:1][CH2:2][C@@H:3]1[CH:18]=[C:17]2[C@@H:7]([CH2:8][C:9]3[C:19]4[C:12](=[CH:13][CH:14]=[CH:15][C:16]2=4)[NH:11][CH:10]=3)[N:5]([CH3:6])[CH2:4]1>C(O)(C)(C)C.FC(F)(F)C(OC(=O)C(F)(F)F)=O>[C:3]([N:11]1[C:12]2[C:19]3[C:9]([CH2:8][C@@H:7]4[C:17]([C:16]=3[CH:15]=[CH:14][CH:13]=2)=[CH:18][C@@H:3]([CH2:2][OH:1])[CH2:4][N:5]4[CH3:6])=[CH:10]1)([CH3:18])([CH3:4])[CH3:2]

Participants

4

Reactant 1

HCID 149871413-67-8

Product 1

HCID 21156211HCID 21156211, compoundYield 122.9%

Reagents, catalysts & solvents 2

HCID 6386tert-ButanolSolventHCID 9845Trifluoroacetic anhydrideSolvent

Procedure

To a mixture of 8 g of lysergol in 150 ml of t-butanol, 200 ml of trifluoroacetic anhydride were added dropwise with vigorous stirring. After the solution had been left at room temperature for 90 hours, it was evaporated. The residue was dissolved in water, made alkaline with ammonium hydroxide and the aqueous layer was extracted with ethyl acetate. After removal of the ethyl acetate, the residue was purified by silica gel column chromatography using 1:1 cyclohexane:ethyl acetate for elution to give 6 g of the title compound melting at 181° to 183° C.

Workup

  1. additionwere added dropwise with vigorous stirring
  2. customit was evaporated
  3. dissolutionThe residue was dissolved in water
  4. extractionthe aqueous layer was extracted with ethyl acetate
  5. customAfter removal of the ethyl acetate
  6. customthe residue was purified by silica gel column chromatography
  7. washethyl acetate for elution

Sources & evidence

ORD record
ord-018c4cb3c78a48df9f21f79c15d632e8
Source dataset
uspto-grants-1989_06
Patent number
US04843073

Reaction notes

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