Sodium Carbonate → 3-[4-(4-Phenyl-piperidin-1-yl)-benzenesulfonylamino]-propionic acid

HRID 378918Notes

Reaction equation

HRID 378918 reaction equation
F[C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:11][CH2:12][CH2:13][C:14]([OH:16])=[O:15])(=[O:10])=[O:9])=[CH:4][CH:3]=1.[Na].Cl.[C:19]1([CH:25]2[CH2:30][CH2:29][NH:28][CH2:27][CH2:26]2)[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.C(=O)([O-])[O-].[Na+].[Na+]>CS(C)=O>[C:19]1([CH:25]2[CH2:26][CH2:27][N:28]([C:2]3[CH:7]=[CH:6][C:5]([S:8]([NH:11][CH2:12][CH2:13][C:14]([OH:16])=[O:15])(=[O:10])=[O:9])=[CH:4][CH:3]=3)[CH2:29][CH2:30]2)[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

6

Reactant 4

HCID 10340Sodium CarbonateHCID 825094-Phenylpiperidinium chlorideHCID 7574113-(4-Fluorobenzenesulfonamido)propanoic acidHCID 5360545Sodium

Product 1

HCID 154328453-[4-(4-Phenyl-piperidin-1-yl)-benzenesulfonylamino]-propionic acid

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
130 °C

Procedure

A stirred mixture of 3-[4-fluoro-(benzenesulfonylamino)]-propionic acid, sodium salt (0.248 g, 0.00100 mol), 4-phenyl-piperidine hydrochloride (0.218 g, 0.00110 mol), and sodium carbonate (0.317 g, 0.00299 mol) in dry dimethyl sulfoxide (3 mL) was heated in a sand bath (130° C.) under nitrogen for 22 hours. The mixture was cooled and partitioned between ethyl acetate and 1 M hydrochloric acid. The aqueous layer was extracted with additional ethyl acetate. The organics were combined, washed with saturated sodium chloride, dried (MgSO4), and rotary evaporated. The residue was dissolved in dichloromethane and chromatographed on silica gel (14 g, 230-400 mesh) eluting with dichloromethane-methanol (15:1, 10×15 mL). Fractions containing product were combined, rotary evaporated and rechromatographed to give the title compound as a peach-colored solid; yield 0.082 g (21%), mp=145-147° C.

Workup

  1. temperatureThe mixture was cooled
  2. custompartitioned between ethyl acetate and 1 M hydrochloric acid
  3. extractionThe aqueous layer was extracted with additional ethyl acetate
  4. washwashed with saturated sodium chloride
  5. dry with materialdried (MgSO4), and rotary evaporated
  6. dissolutionThe residue was dissolved in dichloromethane
  7. customchromatographed on silica gel (14 g, 230-400 mesh)
  8. washeluting with dichloromethane-methanol (15:1, 10×15 mL)
  9. additionFractions containing product
  10. customrotary evaporated
  11. customrechromatographed

Sources & evidence

ORD record
ord-f0c08812dc8945cea32662077624fb8a
Source dataset
uspto-grants-2001_10
Patent number
US06297247B1

Reaction notes

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