Ammonium formate → HCID 22137324, compound

HRID 1827556Notes

Reaction equation

HRID 1827556 reaction equation
C([O:8][C:9]1[CH:14]=[CH:13][C:12]([N:15]([CH2:28][C:29]2[CH:34]=[CH:33][CH:32]=[C:31]([O:35][CH:36]3[CH2:41][CH2:40][CH2:39][CH2:38][O:37]3)[CH:30]=2)[S:16]([C:19]2[C:24]([CH3:25])=[CH:23][C:22]([CH3:26])=[CH:21][C:20]=2[CH3:27])(=[O:18])=[O:17])=[CH:11][CH:10]=1)C1C=CC=CC=1.C([O-])=O.[NH4+]>CO.[Pd]>[OH:8][C:9]1[CH:10]=[CH:11][C:12]([N:15]([CH2:28][C:29]2[CH:34]=[CH:33][CH:32]=[C:31]([O:35][CH:36]3[CH2:41][CH2:40][CH2:39][CH2:38][O:37]3)[CH:30]=2)[S:16]([C:19]2[C:24]([CH3:25])=[CH:23][C:22]([CH3:26])=[CH:21][C:20]=2[CH3:27])(=[O:18])=[O:17])=[CH:13][CH:14]=1

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 22137362HCID 22137362, compound

Product 1

HCID 22137324HCID 22137324, compoundYield 0.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of N-(4-benzyloxy-phenyl)-2,4,6-trimethyl-N-[3-(tetrahydro-pyran-2-yloxy)-benzyl]-benzenesulfonamide (7.39 g, 12.9 mol) in 300 mL methanol was added palladium black (0.800 g) and ammonium formate (8.15 g, 129 mmol). The reaction mixture was heated at reflux for 3 hr. and was cooled. The reaction mixture was filtered through diatomaceous earth with the aid of methanol (2×50 mL). The filtrate was concentrated and the residue was partitioned between 600 mL ethyl acetate and 250 mL water. The layers were separated and the organic layer was washed with water (2×300 mL) and saturated aqueous sodium chloride (1×300 mL). The organic layer was dried (magnesium sulfate), filtered, and concentrated. Medium pressure silica gel chromatography (25% ethyl acetate/hexanes) afforded 5.00 g of the title compound of Step D. MS 482.2 (M+1)+

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux for 3 hr
  3. temperatureand was cooled
  4. filtrationThe reaction mixture was filtered through diatomaceous earth with the aid of methanol (2×50 mL)
  5. concentrationThe filtrate was concentrated
  6. customthe residue was partitioned between 600 mL ethyl acetate and 250 mL water
  7. customThe layers were separated
  8. washthe organic layer was washed with water (2×300 mL) and saturated aqueous sodium chloride (1×300 mL)
  9. dry with materialThe organic layer was dried (magnesium sulfate)
  10. filtrationfiltered
  11. concentrationconcentrated

Sources & evidence

ORD record
ord-10c11e42ef994d7482570315cf406486
Source dataset
uspto-grants-2006_05
Patent number
US07053212B2

Reaction notes

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