4-Toluenesulfonyl chloride → HCID 19028928, compound

HRID 2256340Notes

Reaction equation

HRID 2256340 reaction equation
[CH:1]([NH:3][CH2:4][C:5]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[CH2:6][CH2:7][OH:8])=[O:2].C(N(CC)CC)C.[S:28](Cl)([C:31]1[CH:37]=[CH:36][C:34]([CH3:35])=[CH:33][CH:32]=1)(=[O:30])=[O:29]>C(Cl)Cl.CN(C)C1C=CN=CC=1>[S:28]([C:31]1[CH:37]=[CH:36][C:34]([CH3:35])=[CH:33][CH:32]=1)([O:8][CH2:7][CH2:6][C:5]([C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1)([C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1)[CH2:4][NH:3][CH:1]=[O:2])(=[O:30])=[O:29]

Participants

6

Reactant 3

HCID 73974-Toluenesulfonyl chlorideHCID 8471TriethylamineHCID 19028813HCID 19028813, compound

Product 1

HCID 19028928HCID 19028928, compoundYield 94.7%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To a suspension of 4-formylamino-3,3-diphenylbutanol (21.5 g) in methylene chloride (250 ml) were added triethylamine (22 ml), 4-dimethylaminopyridine (catalyst amount) and tosyl chloride (15.3 g) and the mixture was stirred at room temperature for 16 hours. The reaction mixture was concentrated to dryness and dissolved in water-ethyl acetate. The ethyl acetate layer was washed with 1N-hydrochloric acid, further washed with water, dried over anhydrous sodium sulfate, and concentrated to dryness. The residue was purified by silica gel column chromatography (n-hexane: ethyl acetate 4:1~1:1) to provide the title compound (32 g) as colorless syrup.

Workup

  1. concentrationThe reaction mixture was concentrated to dryness
  2. dissolutiondissolved in water-ethyl acetate
  3. washThe ethyl acetate layer was washed with 1N-hydrochloric acid
  4. washfurther washed with water
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated to dryness
  7. customThe residue was purified by silica gel column chromatography (n-hexane: ethyl acetate 4:1~1:1)

Sources & evidence

ORD record
ord-d8d93940bf344cc0a9d9e5e5ec573bdf
Source dataset
uspto-grants-1997_08
Patent number
US05654296

Reaction notes

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