p-Toluenesulfonic acid monohydrate → HCID 67019962, compound

HRID 1673210Notes

Reaction equation

HRID 1673210 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:9]=[C:10]3[C:25]([CH2:27][C:28]([O:30][CH2:31][CH3:32])=[O:29])(O)[CH2:24][C:23]([CH3:34])([CH3:33])[O:22][C:11]3=[N:12][C:13]=2[C:14]2[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][C:15]=2[Cl:21])=[CH:4][CH:3]=1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1.CCOC(C)=O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[CH:9]=[C:10]3[C:25](=[CH:27][C:28]([O:30][CH2:31][CH3:32])=[O:29])[CH2:24][C:23]([CH3:33])([CH3:34])[O:22][C:11]3=[N:12][C:13]=2[C:14]2[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][C:15]=2[Cl:21])=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 521998p-Toluenesulfonic acid monohydrateHCID 67023905HCID 67023905, compound

Product 1

HCID 67019962HCID 67019962, compound

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
104 °C

Procedure

To the product of Step A this example (192 mg, 0.382 mmol) was added p-toluenesulfonic acid monohydrate (72.6 mg, 0.276 mmol) in toluene (3 mL). The reaction was heated to 104° C. After 80 min the reaction was cooled and diluted with EtOAc. The solution was washed with brine and saturated aq NaHCO3. The concentrated residue was purified by flash chromatography on silica gel gradient eluted with 0-25% EtOAc in hexane affording the title compound as the faster eluting isomer on silica gel. (LC-2) HPLC/MS: 502.1 (M+1), 504.1 (M+3); Rt=4.52 min.

Workup

  1. temperatureAfter 80 min the reaction was cooled
  2. washThe solution was washed with brine and saturated aq NaHCO3
  3. customThe concentrated residue was purified by flash chromatography on silica gel gradient
  4. washeluted with 0-25% EtOAc in hexane affording the title compound as the
  5. washfaster eluting isomer on silica gel

Sources & evidence

ORD record
ord-f902d558a5fd4091bb5688c471267046
Source dataset
uspto-grants-2011_08
Patent number
US07999107B2

Reaction notes

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