Triethylamine → 6-Chloro-2-hydroxy-N,N-dimethyl-3-{2-[(R)-1-((2R,5R)-5-methyl-tetrahydrofuran-2-yl)-propylamino]-3,4-dioxo-cyclobut-1-enylamino}-benzenesulfonamide

HRID 1927568Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1927568
[Cl:1][C:2]1[C:7]([S:8]([N:11]([CH3:13])[CH3:12])(=[O:10])=[O:9])=[C:6]([OH:14])[C:5]([NH:15][C:16]2[C:19](=[O:20])[C:18](=[O:21])[C:17]=2OCC)=[CH:4][CH:3]=1.C1(C)C=CC(S(O)(=O)=O)=CC=1.[CH3:36][C@H:37]1[O:41][C@@H:40]([C@H:42]([NH2:45])[CH2:43][CH3:44])[CH2:39][CH2:38]1.CCN(CC)CC>CC#N>[Cl:1][C:2]1[C:7]([S:8]([N:11]([CH3:12])[CH3:13])(=[O:10])=[O:9])=[C:6]([OH:14])[C:5]([NH:15][C:16]2[C:19](=[O:20])[C:18](=[O:21])[C:17]=2[NH:45][C@@H:42]([C@H:40]2[CH2:39][CH2:38][C@@H:37]([CH3:36])[O:41]2)[CH2:43][CH3:44])=[CH:4][CH:3]=1

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 86638630(R)-1-((2R,5R)-5-methyl-tetrahydro-furan-2-yl)-propylamine para-toluenesulfonate saltHCID 866418016-chloro-3-(2-ethoxy-3,4-dioxo-cyclobut-1-enylamino)-2-hydroxy-N,N-dimethyl-benzenesulfonamide

Produkt 1

HCID 593273546-Chloro-2-hydroxy-N,N-dimethyl-3-{2-[(R)-1-((2R,5R)-5-methyl-tetrahydrofuran-2-yl)-propylamino]-3,4-dioxo-cyclobut-1-enylamino}-benzenesulfonamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

To a stirred solution of 253 mg of 6-chloro-3-(2-ethoxy-3,4-dioxo-cyclobut-1-enylamino)-2-hydroxy-N,N-dimethyl-benzenesulfonamide in 5 ml of dry MeCN are added 362 mg of (R)-1-((2R,5R)-5-methyl-tetrahydrofuran-2-yl)-propylamine p-toluenesulfonate salt followed by 94 μl of Et3N at rt under an inert atmosphere of nitrogen. A reaction mixture obtained is heated at reflux for 45 minutes and solvent is evaporatedA residue obtained is purified by flash chromatography on silica eluting with 30-40% EtOAc in iso-hexane. The title compound is obtained. MH+ 472.

Aufarbeitung

  1. customA reaction mixture obtained
  2. temperatureis heated
  3. temperatureat reflux for 45 minutes
  4. customobtained
  5. customis purified by flash chromatography on silica eluting with 30-40% EtOAc in iso-hexane

Quellen und Nachweise

ORD-Eintrag
ord-603e80b2781d487a99cf582a1db01c88
Quelldatensatz
uspto-grants-2012_05
Patentnummer
US08183281B2

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