Hydrochloric Acid → HCID 1948, compound

HRID 378915Notes

Reaction equation

HRID 378915 reaction equation
F[C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:11][CH2:12][C:13]([OH:15])=[O:14])(=[O:10])=[O:9])=[CH:4][CH:3]=1.[C:16]1([CH:22]2[CH2:27][CH2:26][NH:25][CH2:24][CH2:23]2)[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.C(=O)([O-])[O-].[K+].[K+].Cl>CS(C)=O.CO>[C:16]1([CH:22]2[CH2:23][CH2:24][N:25]([C:2]3[CH:7]=[CH:6][C:5]([S:8]([NH:11][CH2:12][C:13]([OH:15])=[O:14])(=[O:10])=[O:9])=[CH:4][CH:3]=3)[CH2:26][CH2:27]2)[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 698734-PhenylpiperidineHCID 7302692-(4-fluorophenylsulfonamido)acetic acid

Product 1

HCID 1948HCID 1948, compound

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 887MethanolSolvent

Procedure

A stirred mixture of (4-fluoro-benzenesulfonyl-amino)-acetic acid (0.0895 g, 0.000384 mol), 4-phenyl-piperidine (0.618 g, 0.000383 mol), and potassium carbonate (0.109 g, 0.000789 mol) in dry dimethyl sulfoxide (0.10 mL) in a tightly capped vial was placed in a hot sand bath (115° C.). After 21 hours, the reaction mixture was cooled and partitioned between ethyl acetate and water. The mixture was acidified with 1M hydrochloric acid (3.2 mL, 0.0032 mol) and the layers were separated. The aqueous layer was washed with additional ethyl acetate. The organics were combined, dried (MgSO4), and rotary evaporated to give a glass. The glass was dissolved in methanol, silica gel was added (4.2 g, 230-400 mesh), and the mixture was rotary evaporated to dryness. The resulting powder was poured onto a column of silica gel (14 g, 230-400 mesh), and eluted with a mixture of hexanes-ethyl acetate-acetic acid (15:15:1, 11×15 mL). Fractions containing product were combined and rotary evaporated. The residue was crystallized from methanol-water (1:1) after a hot filtration to give the title compound as a pale yellow solid; yield 0.070 g (49%), mp=154.5-155.5° C.

Workup

  1. customwas placed in a hot sand bath
  2. custom(115° C.)
  3. temperaturethe reaction mixture was cooled
  4. custompartitioned between ethyl acetate and water
  5. customthe layers were separated
  6. washThe aqueous layer was washed with additional ethyl acetate
  7. dry with materialdried (MgSO4)
  8. customrotary evaporated
  9. customto give a glass
  10. additionsilica gel was added (4.2 g, 230-400 mesh)
  11. customthe mixture was rotary evaporated to dryness
  12. additionThe resulting powder was poured onto a column of silica gel (14 g, 230-400 mesh)
  13. washeluted with a mixture of hexanes-ethyl acetate-acetic acid (15:15:1, 11×15 mL)
  14. additionFractions containing product
  15. customThe residue was crystallized from methanol-water (1:1)
  16. filtrationafter a hot filtration

Sources & evidence

ORD record
ord-ab078bbe818e48449f30c49368374505
Source dataset
uspto-grants-2001_10
Patent number
US06297247B1

Reaction notes

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