Potassium Carbonate → HCID 57809716, compound

HRID 2388638Notes

Reaction equation

HRID 2388638 reaction equation
[N:1]1([C:6]([O:8][C:9]2[CH:14]=[CH:13][C:12]([CH2:15][C@H:16]([NH:24][C:25]3[C:30]([NH:31][S:32]([CH3:35])(=[O:34])=[O:33])=[CH:29][N:28]=[C:27]([N:36]([CH2:39][CH3:40])[CH2:37][CH3:38])[N:26]=3)[C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])=[CH:11][CH:10]=2)=[O:7])[CH2:5][CH2:4][CH2:3][CH2:2]1.C([O-])([O-])=O.[K+].[K+].[CH2:47](Cl)[C:48]#[CH:49]>CC(C)=O>[N:1]1([C:6]([O:8][C:9]2[CH:14]=[CH:13][C:12]([CH2:15][C@H:16]([NH:24][C:25]3[C:30]([N:31]([CH2:49][C:48]#[CH:47])[S:32]([CH3:35])(=[O:34])=[O:33])=[CH:29][N:28]=[C:27]([N:36]([CH2:37][CH3:38])[CH2:39][CH3:40])[N:26]=3)[C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])=[CH:11][CH:10]=2)=[O:7])[CH2:2][CH2:3][CH2:4][CH2:5]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 122213-Chloro-1-propyneHCID 57809708HCID 57809708, compound

Product 1

HCID 57809716HCID 57809716, compoundYield 51.1%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Compound 11 (0.20 g, 0.35 mmol), K2CO3 (0.073 g, 0.53 mmol), and acetone (3 mL) were placed in a sealed tube and stirred at room temperature for one hour. Propargyl chloride (0.26 mL, 3.5 mmol) was added and the reaction was sealed and heated at reflux for 48 hours. The reaction mixture was concentrated in vacuo and the residue taken up in ethyl acetate. The solution was washed with water and brine. The organic layer was dried over Na2SO4, filtered, and concentrated in vacuo to yield crude product as an orange film. The residue was purified by flash chromatography (1:1 ethyl acetate/hexanes) to yield 0.11 g (51%) of compound 12 as a transparent film.

Workup

  1. customthe reaction was sealed
  2. temperatureheated
  3. temperatureat reflux for 48 hours
  4. concentrationThe reaction mixture was concentrated in vacuo
  5. washThe solution was washed with water and brine
  6. dry with materialThe organic layer was dried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customto yield crude product as an orange film
  10. customThe residue was purified by flash chromatography (1:1 ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-694cd35b04ce42c6a602e6ba0c5a2ecf
Source dataset
uspto-grants-2012_09
Patent number
US08269009B2

Reaction notes

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