Hydroxylamine → n-(4-(1,2,4-Oxadiazol-3-yl)benzyl)-n-(7-hydroxybicyclo[2.2.1]heptan-2-yl)-4-chlorobenzenesulfonamide

HRID 1011550Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1011550
[C:1]([C:3]1[CH:28]=[CH:27][C:6]([CH2:7][N:8]([CH:19]2[CH2:24][CH:23]3[CH:25]([OH:26])[CH:20]2[CH2:21][CH2:22]3)[S:9]([C:12]2[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][CH:13]=2)(=[O:11])=[O:10])=[CH:5][CH:4]=1)#[N:2].[NH2:29]O.C([O:34][CH2:35]C)(=O)C>C(O)C.C(OC(OCC)OCC)C>[O:34]1[CH:35]=[N:29][C:1]([C:3]2[CH:4]=[CH:5][C:6]([CH2:7][N:8]([CH:19]3[CH2:24][CH:23]4[CH:25]([OH:26])[CH:20]3[CH2:21][CH2:22]4)[S:9]([C:12]3[CH:13]=[CH:14][C:15]([Cl:18])=[CH:16][CH:17]=3)(=[O:11])=[O:10])=[CH:27][CH:28]=2)=[N:2]1

Komponenten

6

Edukt 3

HCID 787HydroxylamineHCID 8857Ethyl AcetateHCID 59497811N-(4-cyanobenzyl)-N-(7-hydroxybicyclo[2.2.1]heptan-2-yl)-4-chlorobenzenesulfonamide

Produkt 1

HCID 59497796n-(4-(1,2,4-Oxadiazol-3-yl)benzyl)-n-(7-hydroxybicyclo[2.2.1]heptan-2-yl)-4-chlorobenzenesulfonamideAusbeute 44 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 702EthanolLösungsmittelHCID 31214Ethyl orthoformateLösungsmittel

Versuchsvorschrift

A mixture of N-(4-cyanobenzyl)-N-(7-hydroxybicyclo[2.2.1]heptan-2-yl)-4-chlorobenzenesulfonamide (380 mg, 0.91 mmol) and hydroxylamine (500 up was refluxed in 20 mL ethanol for 2 h. The reaction was concentrated and dried under high vacuum. A portion of the crude amide oxime (25 mg) which was obtained was refluxed in triethylorthoformate (2 mL) for 5 h. The reaction was diluted into 20 mL ethyl acetate, washed with brine, and purified by flash chromatography on 4 g silica gel with 0 to 30% ethyl acetate in hexane to yield N-(4-(1,2,4-oxadiazol-3-yl)benzyl)-N-(7-hydroxybicyclo[2.2.1]heptan-2-yl)-4-chlorobenzenesulfonamide (11 mg, 44%). 1H NMR (400 MHz, CDCl3) δ ppm 8.73 (1H, s), 8.00-8.08 (2H, m), 7.68-7.79 (2H, m), 7.40-7.49 (4H, m), 4.83 (2H, q, J=17.54 Hz), 4.02-4.11 (1H, m), 3.83 (1H, s), 1.88 (1H, br. s.), 1.58-1.68 (2H, m), 1.43-1.55 (3H, m), 1.06-1.16 (2H, m). LC/MS R.T.=2.35 min; [M+H]+=460.13.

Aufarbeitung

  1. concentrationThe reaction was concentrated
  2. customdried under high vacuum
  3. customA portion of the crude amide oxime (25 mg) which was obtained
  4. washwashed with brine
  5. custompurified by flash chromatography on 4 g silica gel with 0 to 30% ethyl acetate in hexane

Quellen und Nachweise

ORD-Eintrag
ord-e0090dc6e1af461d8c69d440d7a7ef16
Quelldatensatz
uspto-grants-2011_07
Patentnummer
US07977362B2

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