Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1) → HCID 58123536, compound

HRID 536670Notes

Reaction equation

HRID 536670 reaction equation
O[C:2]1[C:3]([NH:24][C:25]([CH:27]2[CH2:29][CH2:28]2)=[O:26])=[CH:4][C:5]2[C@@:12]3([CH3:16])[C:13]([CH3:15])([CH3:14])[C@H:8]([N:9]([C:17](=[O:22])[C:18]([F:21])([F:20])[F:19])[CH2:10][CH2:11]3)[CH2:7][C:6]=2[CH:23]=1.C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1>C1(C)C(C)=CC=CC=1>[CH:27]1([C:25]2[O:26][C:2]3[C:3]([N:24]=2)=[CH:4][C:5]2[C@@:12]4([CH3:16])[C:13]([CH3:14])([CH3:15])[C@@H:8]([CH2:7][C:6]=2[CH:23]=3)[N:9]([C:17](=[O:22])[C:18]([F:21])([F:20])[F:19])[CH2:10][CH2:11]4)[CH2:28][CH2:29]1

Participants

4

Reactant 2

HCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 58123695HCID 58123695, compound

Product 1

HCID 58123536HCID 58123536, compound

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

A solution of cyclopropanecarboxylic acid [(2R,6S)-9-hydroxy-6,11,11-trimethyl-3-(2,2,2-trifluoro-acetyl)-1,2,3,4,5,6-hexahydro-2,6-methano-benzo[d]azocin-8-yl]-amide (0.62 g) and pyridinium p-toluenesulfonate (76 mg) in xylene (6 mL) is stirred at reflux temperature for 5 h. After cooling to room temperature, the solution is concentrated, ethyl acetate is added to the residue, and the resulting mixture is washed with water and brine. The organic solution is dried (MgSO4) and the solvent is evaporated to afford the title compound.

Workup

  1. temperatureat reflux temperature for 5 h
  2. concentrationthe solution is concentrated
  3. additionethyl acetate is added to the residue
  4. washthe resulting mixture is washed with water and brine
  5. dry with materialThe organic solution is dried (MgSO4)
  6. customthe solvent is evaporated

Sources & evidence

ORD record
ord-2418a693fa1645a1a788eaf83133f18c
Source dataset
uspto-grants-2014_10
Patent number
US08859580B2

Reaction notes

Loading…