Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1) → HCID 59253305, compound

HRID 386889Notes

Reaction equation

HRID 386889 reaction equation
[C:1]([O:5][C:6](=[O:24])[NH:7][C:8]1[O:12][N:11]=[C:10]([C:13]([CH3:23])([CH3:22])[CH2:14][O:15]C2CCCCO2)[CH:9]=1)([CH3:4])([CH3:3])[CH3:2].C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1>C(O)C>[C:1]([O:5][C:6](=[O:24])[NH:7][C:8]1[O:12][N:11]=[C:10]([C:13]([CH3:23])([CH3:22])[CH2:14][OH:15])[CH:9]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 59253304{3-[1,1-Dimethyl-2-(tetrahydro-pyran-2-yloxy)-ethyl]-isoxazol-5-yl}-carbamic acid tert-butyl ester

Product 1

HCID 59253305HCID 59253305, compoundYield 85.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 933.0 mg (2.74 mmol) of {3-[1,1-dimethyl-2-(tetrahydro-pyran-2-yloxy)-ethyl]-isoxazol-5-yl}-carbamic acid tert-butyl ester and 103.0 mg (0.41 mmol) of pyridinium p-toluenesulfonate in ethanol (8.0 mL) is stirred at 65° C. for 1 h. After this time, the reaction mixture is concentrated under reduced pressure. Purification by flash chromatography on silica gel using ethyl acetate/heptane provides 602.0 mg of the title compound. Yield: 85.7%. 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 1.3 (6H, s), 1.55 (9H, s), 2.35 (1H, t, J=8.0 Hz), 3.7 (2H, d, J=8.0 Hz), 6.5 (1H, s), 7.3 (1H, s).

Workup

  1. concentrationAfter this time, the reaction mixture is concentrated under reduced pressure
  2. customPurification by flash chromatography on silica gel

Sources & evidence

ORD record
ord-2c3ab9103148475898ff3aee7cb0f776
Source dataset
uspto-grants-2013_02
Patent number
US08372874B2

Reaction notes

Loading…