Benzenesulfonyl chloride → Hexanoic acid, 6-[(phenylsulfonyl)amino]-, methyl ester

HRID 351093

Reaktionsgleichung

Reaktionsgleichung von HRID 351093
[C:1]1([S:7](Cl)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl.[NH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][C:18]([O:20][CH3:21])=[O:19].C(=O)([O-])[O-].[Na+].[Na+]>C(#N)C.O>[CH3:21][O:20][C:18](=[O:19])[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][NH:12][S:7]([C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)(=[O:9])=[O:8]

Komponenten

6

Edukt 3

HCID 7369Benzenesulfonyl chlorideHCID 10340Sodium CarbonateHCID 11499324Methyl 6-aminohexanoate hydrochloride

Produkt 1

HCID 15295437Hexanoic acid, 6-[(phenylsulfonyl)amino]-, methyl ester

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

Benzenesulfonyl chloride (92a) (0.88 g, 5.0 mmol) was added to the mixture of methyl 6-aminohexanoate hydrochloride (91) (1.82 g, 10 mmol) in acetonitrile (10 ml) and sodium carbonate (2.6 g, 24.6 mmol) in water (10 ml). The mixture was stirred for 6 hours at ambient temperature, and the product was extracted with ethyl acetate (30 ml). The extract was dried (Na2SO4) and solvents were removed under reduced pressure. The product was chromatographed on silica gel with ethyl acetate-hexane (1:2) as eluent. The title compound was obtained as oil (1.28 g, 90%). 1H NMR δH (90 MHz, DMSO-d6) δ: 0.90–1.63 (6H, m, CH2); 2.21 (2H, t, J=7.0 Hz, CH2); 2.71 (2H, q, J=6.0 Hz, CH2N); 3.58 (3H, s, CH3); 7.40–7.72 (3H, m, C6H3); 7.72–7.89 (2H, m, C6H2).

Aufarbeitung

  1. extractionthe product was extracted with ethyl acetate (30 ml)
  2. dry with materialThe extract was dried (Na2SO4) and solvents
  3. customwere removed under reduced pressure
  4. customThe product was chromatographed on silica gel with ethyl acetate-hexane (1:2) as eluent

Quellen und Nachweise

ORD-Eintrag
ord-38fe20f6332d4c4e924b82cd75dd348c
Quelldatensatz
uspto-grants-2007_02
Patentnummer
US07183298B2

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