Boron trifluoride etherate → HCID 22803978, compound

HRID 866326Notes

Reaction equation

HRID 866326 reaction equation
[O:1]([CH3:21])[C:2]([C@@H:4]1[CH:19]=[C:18]2[C@@H:8]([CH2:9][CH:10]3[C:20]4[C:13](=[CH:14][CH:15]=[CH:16][C:17]2=4)[NH:12][CH2:11]3)[N:6]([CH3:7])[CH2:5]1)=[O:3].B(F)(F)F.CCOCC.S(Cl)([Cl:34])(=O)=O>C(Cl)Cl>[Cl:34][CH:11]1[NH:12][C:13]2[C:20]3[CH:10]1[CH2:9][C@@H:8]1[C:18]([C:17]=3[CH:16]=[CH:15][CH:14]=2)=[CH:19][C@@H:4]([C:2](=[O:3])[O:1][CH3:21])[CH2:5][N:6]1[CH3:7]

Participants

5

Reactant 3

HCID 8000Boron trifluoride etherateHCID 24648Sulfuryl chlorideHCID 22791380HCID 22791380, compound

Product 1

HCID 22803978HCID 22803978, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

885 mg. of methyl dihydrolysergate were dissolved in 50 ml. of methylene dichloride. 0.95 ml. of boron trifluoride etherate were added and the reaction mixture cooled to a temperature in the range 0°-5° C. A solution of 0.27 ml. sulfuryl chloride in 20 ml. of methylene dichloride was added in dropwise fashion. The reaction mixture was stirred and cooled for about 15 minutes and then quenched by pouring into an ice-dilute ammonium hydroxide mixture. D-2-chloro-6-methyl-8-carboxyergoline, methyl ester or methyl 2-chlorodihydrolysergate formed in the above reaction was isolated and purified by the procedure of Example 1. Chromatography over fluorosil using 2 percent methanol in chloroform yielded 730 mg. (74 percent yield) of crystalline material melting at 206°-8° C. with decomposition.

Workup

  1. temperaturethe reaction mixture cooled to a temperature in the range 0°-5° C
  2. temperaturecooled for about 15 minutes
  3. customquenched
  4. additionby pouring into an ice-dilute ammonium hydroxide mixture

Sources & evidence

ORD record
ord-0720e4fc70234c2ab4158727b3049718
Source dataset
uspto-grants-1978_07
Patent number
US04098790

Reaction notes

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