4-Toluenesulfonyl chloride → HCID 20590354, compound

HRID 413661Notes

Reaction equation

HRID 413661 reaction equation
C(=O)([O-])[O-].[K+].[K+].[S:7](Cl)([C:10]1[CH:16]=[CH:15][C:13]([CH3:14])=[CH:12][CH:11]=1)(=[O:9])=[O:8].[CH3:18][O:19][C@H:20]1[C@H:25]([OH:26])[C@@H:24]([OH:27])[C@H:23]([N:28]2[C:37]3[C:38]4[NH:46][C:45]5[C:44]([Cl:47])=[CH:43][CH:42]=[CH:41][C:40]=5[C:39]=4[C:48]4[C:53](=[O:54])[NH:52][C:50](=[O:51])[C:49]=4[C:36]=3[C:30]3[CH:31]=[CH:32][CH:33]=[C:34]([Cl:35])[C:29]2=3)[O:22][C@@H:21]1[CH2:55][OH:56]>O1CCCC1>[Cl:47][C:44]1[C:45]2[NH:46][C:38]3[C:37]4[N:28]([C@@H:23]5[O:22][C@H:21]([CH2:55][OH:56])[C@@H:20]([O:19][CH3:18])[C@H:25]([OH:26])[C@H:24]5[O:27][S:7]([C:10]5[CH:16]=[CH:15][C:13]([CH3:14])=[CH:12][CH:11]=5)(=[O:9])=[O:8])[C:29]5[C:30](=[CH:31][CH:32]=[CH:33][C:34]=5[Cl:35])[C:36]=4[C:49]4[C:50](=[O:51])[NH:52][C:53](=[O:54])[C:48]=4[C:39]=3[C:40]=2[CH:41]=[CH:42][CH:43]=1

Participants

5

Reactant 3

HCID 73974-Toluenesulfonyl chlorideHCID 11430Potassium CarbonateHCID 73110Rebeccamycin

Product 1

HCID 20590354HCID 20590354, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1 equivalent of potassium carbonate and 1 equivalent of tosyl chloride are added to a solution of 1.7 mmol of rebeccamycin in 200 ml of tetrahydrofuran. After 48 hours' reflux and concentration under reduced pressure, chromatography of the residue over silica gel (cyclohexane/ethyl acetate 70/30) enables the expected product to be isolated.

Workup

  1. temperatureAfter 48 hours' reflux
  2. concentrationconcentration under reduced pressure, chromatography of the residue over silica gel (cyclohexane/ethyl acetate 70/30)
  3. customto be isolated

Sources & evidence

ORD record
ord-72192b0639994cef88f0ad8e22862204
Source dataset
uspto-grants-2003_05
Patent number
US06569858B2

Reaction notes

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