Potassium Carbonate → HCID 14277566, compound

HRID 1461750Notes

Reaction equation

HRID 1461750 reaction equation
[CH2:1]([N:4]1[C@H:18]2[C@@H:8]([C:9]3[CH:10]=[CH:11][CH:12]=[C:13]4[C:19]=3[C:16]([CH2:17]2)=[CH:15][NH:14]4)[CH2:7][C@H:6]([NH:20][C:21](=[O:26])[C:22]([CH3:25])([CH3:24])[CH3:23])[CH2:5]1)[CH2:2][CH3:3].S(Cl)([Cl:30])(=O)=O.C(=O)([O-])[O-].[K+].[K+]>C(Cl)Cl>[Cl:30][C:15]1[NH:14][C:13]2[C:19]3[C:16]=1[CH2:17][C@@H:18]1[C@@H:8]([C:9]=3[CH:10]=[CH:11][CH:12]=2)[CH2:7][C@H:6]([NH:20][C:21](=[O:26])[C:22]([CH3:25])([CH3:24])[CH3:23])[CH2:5][N:4]1[CH2:1][CH2:2][CH3:3]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 24648Sulfuryl chlorideHCID 14277505HCID 14277505, compound

Product 1

HCID 14277566HCID 14277566, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

1 g silica gel are added to 2 g 6-n-propyl-8α-pivaloylamino-ergoline (example 2) in 50 ml methylene chloride, pre-cooled to 0° C. 0.503 ml sulfurylchloride are added drop-wise and the reaction mixture stirred for 4 hours. 1N potassium carbonate solution is added, the mixture extracted with methylene chloride, dried over Na2SO4 and concentrated. The residue is chromatographed on 50 g silica gel using toluene/ethylacetate (2:1) as eluant to yield the title compound. M.P.=146°-147° C.

Workup

  1. extractionthe mixture extracted with methylene chloride
  2. dry with materialdried over Na2SO4
  3. concentrationconcentrated
  4. customThe residue is chromatographed on 50 g silica gel

Sources & evidence

ORD record
ord-8c7942d8fec9465eb6b4fe6712ab059a
Source dataset
uspto-grants-1991_12
Patent number
US05077298

Reaction notes

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