MeOH tetrahydrofuran → HCID 15432844, compound

HRID 378917Notes

Reaction equation

HRID 378917 reaction equation
[C:1]1([CH:7]2[CH2:12][CH2:11][N:10]([C:13]3[CH:18]=[CH:17][C:16]([S:19]([NH:22][CH2:23][C:24]([NH2:26])=[O:25])(=[O:21])=[O:20])=[CH:15][CH:14]=3)[CH2:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CO.[O:29]1CCCC1>C(Cl)(Cl)Cl.CO.[Pd]>[OH:29][NH:26][C:24](=[O:25])[CH2:23][NH:22][S:19]([C:16]1[CH:17]=[CH:18][C:13]([N:10]2[CH2:11][CH2:12][CH:7]([C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)[CH2:8][CH2:9]2)=[CH:14][CH:15]=1)(=[O:20])=[O:21]

Participants

5

Reactant 2

HCID 21899815MeOH tetrahydrofuranHCID 86756066HCID 86756066, compound

Product 1

HCID 15432844HCID 15432844, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 21584188Chloroform methanolSolvent

Procedure

A room temperature mixture of N-[phenyl-methyl)oxy]-2-[4-(4-phenyl-piperidin-1-yl)-benzenesulfonylamino]-acetamide (0.1115 g, 0.0002325 mol) in methanol-tetrahydrofuran (1:1, 25 mL) was hydrogenated at 50 p.s.i. over 5% palladium on barium sulfate (0.018 g) for approximately 10 hours Additional catalyst (0.020 g) was added, and the mixture hydrogenated again for approximately 10 hours. The mixture was filtered through celite, and the filtrate was rotary evaporated to give a glaze. The glaze was dissolved in chloroform-methanol, silica gel (1.6 g, 230-400 mesh) was added, and the mixture was rotary evaporated to dryness. The powder was poured onto a column of silica gel (10 g, 230-400 mesh) and eluted with hexanes-ethyl acetate-acetic acid (10:20:1, 16×10 mL and 10:20:2, 16×10 mL). Fractions containing product were rotary evaporated, and the residue triturated with chloroform. The chloroform suspension was filtered, and the filtercake was dried in vacuo; yield 0.0054 g (6.0%), mp=164-166° C.

Workup

  1. filtrationThe mixture was filtered through celite
  2. customthe filtrate was rotary evaporated
  3. customto give a glaze
  4. additionsilica gel (1.6 g, 230-400 mesh) was added
  5. customthe mixture was rotary evaporated to dryness
  6. additionThe powder was poured onto a column of silica gel (10 g, 230-400 mesh)
  7. washeluted with hexanes-ethyl acetate-acetic acid (10:20:1, 16×10 mL and 10:20:2, 16×10 mL)
  8. additionFractions containing product
  9. customthe residue triturated with chloroform
  10. filtrationThe chloroform suspension was filtered
  11. customthe filtercake was dried in vacuo

Sources & evidence

ORD record
ord-460f86da7bd24a9daebccaae28367edb
Source dataset
uspto-grants-2001_10
Patent number
US06297247B1

Reaction notes

Loading…