6-Aminohexanoic Acid → 6-((Phenylsulphonyl)amino)hexanoic acid

HRID 2103983Notes

Reaction equation

HRID 2103983 reaction equation
[C:1]1([S:7](Cl)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[NH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][C:17]([OH:19])=[O:18]>[OH-].[Na+].O1CCOCC1>[C:1]1([S:7]([NH:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][C:17]([OH:19])=[O:18])(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 2

HCID 5646-Aminohexanoic AcidHCID 7369Benzenesulfonyl chloride

Product 1

HCID 30172786-((Phenylsulphonyl)amino)hexanoic acidYield 55%

Reagents, catalysts & solvents 2

HCID 14798Sodium HydroxideSolventHCID 312751,4-DioxaneSolvent

Procedure

Benzenesulfonyl chloride (2.5 ml, 19 mmol) was added to a solution of 6-aminohexanoic acid (1 g, 7.62 mmol) in 2N NaOH (22 ml) and dioxane (3 ml), while stirring at 0° C.-5° C. The mixture was allowed to warm to room temperature and stirred for 1 hour. The reaction mixture was washed with ethyl acetate (50 ml), then acidified to pH 2 with 37% hydrochloric acid and extracted with ethyl acetate (2×50 ml). The combined organic layers were dried over sodium sulfate and concentrated. The residue was triturated with hexane. The solid was collected by filtration and dried under vacuum at 50° C. affording 1.1 g of the title compound (55% yield).

Workup

  1. stirringstirred for 1 hour
  2. washThe reaction mixture was washed with ethyl acetate (50 ml)
  3. extractionextracted with ethyl acetate (2×50 ml)
  4. dry with materialThe combined organic layers were dried over sodium sulfate
  5. concentrationconcentrated
  6. customThe residue was triturated with hexane
  7. filtrationThe solid was collected by filtration
  8. customdried under vacuum at 50° C.

Sources & evidence

ORD record
ord-1f308bff7beb4bd8a17d06bc5e09aa2e
Source dataset
uspto-grants-2009_08
Patent number
US07576206B2

Reaction notes

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