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

HRID 556297
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 556297
[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
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 2

HCID 5646-Aminohexanoic AcidHCID 7369Benzenesulfonyl chloride

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 14798Sodium HydroxideLösungsmittelHCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

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).

Aufarbeitung

  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.

Quellen und Nachweise

ORD-Eintrag
ord-954bbb0c07c04957b5ed838af35157cc
Quelldatensatz
uspto-grants-2011_11
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08058262B2

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