Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1) → HCID 45110125, compound

HRID 386901Notes

Reaction equation

HRID 386901 reaction equation
[CH3:1][C:2]([C:13]1[CH:17]=[C:16]([NH:18][C:19](=[O:32])[C:20]([CH3:31])([S:22]([CH:25]2[CH2:30][CH2:29][O:28][CH2:27][CH2:26]2)(=[O:24])=[O:23])[CH3:21])[O:15][N:14]=1)([CH3:12])[C@@H:3]([O:5]C1CCCCO1)[CH3:4].C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1>C(O)C>[OH:5][C@@H:3]([CH3:4])[C:2]([C:13]1[CH:17]=[C:16]([NH:18][C:19](=[O:32])[C:20]([CH3:31])([S:22]([CH:25]2[CH2:26][CH2:27][O:28][CH2:29][CH2:30]2)(=[O:24])=[O:23])[CH3:21])[O:15][N:14]=1)([CH3:12])[CH3:1]

Participants

4

Reactant 2

HCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 45110628HCID 45110628, compound

Product 1

HCID 45110125HCID 45110125, compoundYield 76.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of N-{3-[(S)-1,1-Dimethyl-2-(tetrahydro-pyran-2-yloxy)-propyl]-isoxazol-5-yl}-2-methyl-2-(tetrahydro-pyran-4-sulfonyl)-propionamide (1.14 g, 2.41 mmol) and pyridinium p-toluenesulfonate (120.63 mg, 0.48 mmol) in ethanol (11 mL) is stirred at 65° C. for 3 h. After this time, the reaction mixture is concentrated under reduced pressure and partitioned between ethyl acetate and water. The layers are separated and the aqueous layer is extracted with ethyl acetate once. The organic extracts are combined and washed with brine, dried over Na2SO4, filtered and concentrated. The resulting solid is trituated in ethanol and filtered to yield the title compound. Yield 76.4%; (400 MHz, CHLOROFORM-d) δ ppm 1.15 (3H, d), 1.28 (6H, s), 1.72 (6H, s), 1.80-1.90 (2H, m), 1.90-2.02 (2H, m), 2.26 (1H, d), 3.32-3.43 (2H, m), 3.40-3.50 (1H, m), 3.85-3.93 (1H, m), 4.00-4.10 (2H, m), 6.29 (1H, s), 9.62 (1H, s). ES-MS: m/z 389 [M+H].

Workup

  1. concentrationAfter this time, the reaction mixture is concentrated under reduced pressure
  2. custompartitioned between ethyl acetate and water
  3. customThe layers are separated
  4. extractionthe aqueous layer is extracted with ethyl acetate once
  5. washwashed with brine
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. filtrationfiltered

Sources & evidence

ORD record
ord-c544f0cdde154745aeda4ee0bba3ec6b
Source dataset
uspto-grants-2013_02
Patent number
US08372874B2

Reaction notes

Loading…