4-Toluenesulfonyl chloride → HCID 18979281, compound

HRID 2393172Notes

Reaction equation

HRID 2393172 reaction equation
[NH2:1][CH:2]([C:12]1[CH:21]=[CH:20][C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[CH:13]=1)[CH2:3][CH2:4][CH2:5][CH2:6][C:7]([O:9][CH2:10][CH3:11])=[O:8].[CH3:22][C:23]1[CH:28]=[CH:27][C:26]([S:29](Cl)(=[O:31])=[O:30])=[CH:25][CH:24]=1.C(N(CC)CC)C>C1COCC1.O>[CH3:22][C:23]1[CH:28]=[CH:27][C:26]([S:29]([NH:1][CH:2]([C:12]2[CH:21]=[CH:20][C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[CH:13]=2)[CH2:3][CH2:4][CH2:5][CH2:6][C:7]([O:9][CH2:10][CH3:11])=[O:8])(=[O:31])=[O:30])=[CH:25][CH:24]=1

Participants

6

Reactant 3

HCID 73974-Toluenesulfonyl chlorideHCID 8471TriethylamineHCID 18979156HCID 18979156, compound

Product 1

HCID 18979281HCID 18979281, compoundYield 84.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution (10 ml) of ethyl 6-amino-6-(2-naphthyl)hexanoate (1.0 g) and 4-methylbenzenesulfonyl chloride (0.73 g) in THF was added triethylamine (0.39 g) dropwise and the mixture was stirred at room temperature for 2 hours. The reaction mixture was then diluted with water and extracted with ethyl acetate. The extract was dried and concentrated and the crude residue was recrystallized from ethyl acetate-hexane to provide the title compound (1.3 g).

Workup

  1. extractionextracted with ethyl acetate
  2. customThe extract was dried
  3. concentrationconcentrated
  4. customthe crude residue was recrystallized from ethyl acetate-hexane

Sources & evidence

ORD record
ord-fb569e552e0a442483f1df3111b828c2
Source dataset
uspto-grants-1998_09
Patent number
US05804601

Reaction notes

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