Potassium Carbonate → HCID 68236280, compound

HRID 409590Notes

Reaction equation

HRID 409590 reaction equation
[Ca].[C:2]([O:6][C:7]([NH:9][CH:10]1[CH2:14][CH2:13][NH:12][CH2:11]1)=[O:8])([CH3:5])([CH3:4])[CH3:3].F[C:16]1[CH:21]=[CH:20][C:19]([S:22]([N:25]([CH3:27])[CH3:26])(=[O:24])=[O:23])=[CH:18][CH:17]=1.C(=O)([O-])[O-].[K+].[K+]>CS(C)=O.C(OCC)(=O)C.O>[CH3:26][N:25]([CH3:27])[S:22]([C:19]1[CH:18]=[CH:17][C:16]([N:12]2[CH2:13][CH2:14][C@H:10]([NH:9][C:7](=[O:8])[O:6][C:2]([CH3:5])([CH3:3])[CH3:4])[CH2:11]2)=[CH:21][CH:20]=1)(=[O:23])=[O:24]

Participants

8

Reactant 4

HCID 11430Potassium CarbonateHCID 7993014-fluoro-N,N-dimethylbenzenesulfonamideHCID 2757234tert-butyl N-(pyrrolidin-3-yl)carbamateHCID 5460341Calcium

Product 1

HCID 68236280HCID 68236280, compound

Reagents, catalysts & solvents 3

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
130 °C

Procedure

A solution of 50 g of 4-fluorobenzenesulfonyl chloride in 250 ml of THF was cooled to 0° C., and then, 100 ml of an aqueous 50% dimethylamine solution was added dropwise thereto, and the mixture was stirred at room temperature for 1 day. To the reaction mixture were added water and ethyl acetate, the mixture was stirred and then the liquids were separated. The organic layer was washed with a saturated aqueous sodium bicarbonate solution and dried, the solvent was evaporated, and disopropyl ether and hexane were added to the residue. Then, the precipitates were collected by filtration and washed with hexane to obtain 49.9 g of 4-fluoro-N,N-dimethyl-benzenesulfonamide. (2) In 600 ml of DMSO were suspended 25 g of (S)-(+3-(tert-butoxycarbonylamino)pyrrolidine, 47.9 g of 4-fluoro-N,N-dimethyl-benzenesulfonamide and 139 g of potassium carbonate, and the mixture was stirred at 130° C. for 1 day. To the reaction mixture were added water and ethyl acetate, the resulting mixture was stirred and the liquids were separated. The organic layer was washed with water, and then dried, and the solvent was evaporated. The residue was dissolved in chloroform, NH silica gel was added thereto and the mixture was allowed to stand for a while, and silica gel was filtered off. The silica gel was further washed with ethyl acetate. The filtrate and the washed solution were combined, and the residue obtained by concentration under reduced pressure was purified by silica gel column chromatography (hexane:ethyl acetate=80:20→67:33) to obtain 8.39 g of tert-butyl [(S)-1-(4-dimethylsulfamoylphenyl)-pyrrolidin-3-yl]carbamate.

Workup

  1. stirringthe resulting mixture was stirred
  2. customthe liquids were separated
  3. washThe organic layer was washed with water
  4. customdried
  5. customthe solvent was evaporated
  6. dissolutionThe residue was dissolved in chloroform
  7. additionNH silica gel was added
  8. filtrationwas filtered off
  9. washThe silica gel was further washed with ethyl acetate
  10. customthe residue obtained by concentration under reduced pressure
  11. customwas purified by silica gel column chromatography (hexane:ethyl acetate=80:20→67:33)

Sources & evidence

ORD record
ord-20f944f717b14820a46e9cfad50c2ba4
Source dataset
uspto-grants-2014_06
Patent number
US08759387B2

Reaction notes

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