4-Toluenesulfonyl chloride → HCID 23598857, compound

HRID 891008Notes

Reaction equation

HRID 891008 reaction equation
[C@@H:1]1([N:12]2[C:23]3[C:15](=[C:16]4[C:30](=[O:31])[NH:29][C:28](=[O:32])[C:17]4=[C:18]4[C:22]=3[NH:21][C:20]3[N:24]=[CH:25][CH:26]=[CH:27][C:19]4=3)[C:14]3[CH:33]=[CH:34][CH:35]=[N:36][C:13]2=3)[O:9][C@H:8]([CH2:10][OH:11])[C@@H:6]([OH:7])[C@H:4]([OH:5])[C@H:2]1[OH:3].C(=O)([O-])[O-].[K+].[K+].[C:43]1([CH3:53])[CH:48]=[CH:47][C:46]([S:49](Cl)(=[O:51])=[O:50])=[CH:45][CH:44]=1>O1CCCC1>[S:49]([O:3][C@@H:2]1[C@@H:4]([OH:5])[C@H:6]([OH:7])[C@@H:8]([CH2:10][OH:11])[O:9][C@H:1]1[N:12]1[C:23]2[C:15](=[C:16]3[C:30](=[O:31])[NH:29][C:28](=[O:32])[C:17]3=[C:18]3[C:22]=2[NH:21][C:20]2[N:24]=[CH:25][CH:26]=[CH:27][C:19]3=2)[C:14]2[CH:33]=[CH:34][CH:35]=[N:36][C:13]1=2)([C:46]1[CH:47]=[CH:48][C:43]([CH3:53])=[CH:44][CH:45]=1)(=[O:51])=[O:50]

Participants

5

Reactant 3

HCID 73974-Toluenesulfonyl chlorideHCID 11430Potassium CarbonateHCID 23598855HCID 23598855, compound

Product 1

HCID 23598857HCID 23598857, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of the compound of Example 12 (0.17 mmol) in 10 ml of tetrahydrofuran there are added 23.5 mg of potassium carbonate and 1.7 mmol of para-toluenesulphonic acid chloride. The mixture is heated at reflux for 48 hours. After evaporating off the solvent, the residue is taken up in a water/ethyl acetate mixture and is then filtered over a frit. The crystals are successively washed with ethyl acetate and then with methanol, allowing the expected product to be isolated.

Workup

  1. temperatureThe mixture is heated
  2. temperatureat reflux for 48 hours
  3. customAfter evaporating off the solvent
  4. filtrationis then filtered over a frit
  5. washThe crystals are successively washed with ethyl acetate
  6. customto be isolated

Sources & evidence

ORD record
ord-9cfe3b5213b84be7a79c6bea2a1865bb
Source dataset
uspto-grants-2006_02
Patent number
US07001906B2

Reaction notes

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