4-Toluenesulfonyl chloride → HCID 86585315, compound

HRID 651507Notes

Reaction equation

HRID 651507 reaction equation
[S:1](Cl)([C:4]1[CH:10]=[CH:9][C:7]([CH3:8])=[CH:6][CH:5]=1)(=[O:3])=[O:2].CN(C1C=CC=CN=1)C.[OH:21][CH2:22][CH2:23][O:24][CH2:25][CH2:26][O:27][C:28]1[CH:33]=[CH:32][C:31]([C@H:34]2[CH2:51][C@@:49]3([CH3:50])[C@@H:45]([CH2:46][CH2:47][C:48]3=[O:52])[C@H:44]3[C:35]2=[C:36]2[C:41]([CH2:42][CH2:43]3)=[CH:40][C:39](=[O:53])[CH2:38][CH2:37]2)=[CH:30][CH:29]=1>N1C=CC=CC=1>[CH3:8][C:7]1[CH:9]=[CH:10][C:4]([S:1]([O:21][CH2:22][CH2:23][O:24][CH2:25][CH2:26][O:27][C:28]2[CH:33]=[CH:32][C:31]([C@H:34]3[CH2:51][C@@:49]4([CH3:50])[C@@H:45]([CH2:46][CH2:47][C:48]4=[O:52])[C@H:44]4[C:35]3=[C:36]3[C:41]([CH2:42][CH2:43]4)=[CH:40][C:39](=[O:53])[CH2:38][CH2:37]3)=[CH:30][CH:29]=2)(=[O:3])=[O:2])=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 73974-Toluenesulfonyl chloride2×HCID 218852-DimethylaminopyridineHCID 70019684HCID 70019684, compound

Product 1

HCID 86585315HCID 86585315, compoundYield 76.7%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

320 mg of tosyl chloride and 70 mg of dimethylamino-pyridine are added to 690 mg of the product obtained in Stage D in 5 cm3 of pyridine, then two lots of 115 mg of tosyl chloride is added again. Agitation is carried out for 2 hours and 30 minutes, followed by acidifying with 6N hydrochloric acid, extraction with ethyl acetate, washing with an aqueous solution of sodium bicarbonate, with salt water, drying and evaporating the solvent under reduced pressure, the residue is chromatographed on silica (eluant: ethyl acetate-essence G 7-3 then ethyl acetate). 710 mg of expected product is obtained.

Workup

  1. extractionby acidifying with 6N hydrochloric acid, extraction with ethyl acetate
  2. washwashing with an aqueous solution of sodium bicarbonate, with salt water
  3. customdrying
  4. customevaporating the solvent under reduced pressure
  5. customthe residue is chromatographed on silica (eluant

Sources & evidence

ORD record
ord-1921952bad2944d19091eeac2393f009
Source dataset
uspto-grants-2001_08
Patent number
US06281204B1

Reaction notes

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