Hydrochloric Acid → 5-[1-Fluoro-3-hydroxy-7-(4-formyl-4-methyl-pentyl)-naphthalen-2-yl]-1,1-dioxo-[1,2,5]thiadiazolidin-3-one

HRID 889284Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 889284
[F:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([CH2:12][CH2:13][CH2:14][C:15]([CH3:19])([CH3:18])[CH2:16][OH:17])[CH:10]=2)[CH:5]=[C:4]([OH:20])[C:3]=1[N:21]1[S:25](=[O:27])(=[O:26])[NH:24][C:23](=[O:28])[CH2:22]1.C(N(CC)CC)C.O.Cl>CS(C)=O>[F:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([CH2:12][CH2:13][CH2:14][C:15]([CH:16]=[O:17])([CH3:19])[CH3:18])[CH:10]=2)[CH:5]=[C:4]([OH:20])[C:3]=1[N:21]1[S:25](=[O:26])(=[O:27])[NH:24][C:23](=[O:28])[CH2:22]1

Komponenten

6

Edukt 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 8471TriethylamineHCID 177472965-[1-Fluoro-3-hydroxy-7-(5-hydroxy-4,4-dimethylpentyl)-naphthalen-2-yl]-1,1-dioxo-1,2,5-thiadiazolidin-3-one

Produkt 1

HCID 177475235-[1-Fluoro-3-hydroxy-7-(4-formyl-4-methyl-pentyl)-naphthalen-2-yl]-1,1-dioxo-[1,2,5]thiadiazolidin-3-one

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 679Dimethyl SulfoxideLösungsmittel2×

Versuchsvorschrift

To a stirred solution of 5-[1-fluoro-3-hydroxy-7-(5-hydroxy-4,4-dimethylpentyl)-naphthalen-2-yl]-1,1-dioxo-1,2,5-thiadiazolidin-3-one (1.00 g, 2.23 mmol) in anhydrous DMSO (10 ml) at room temperature was added triethylamine (2.17 mL, 15.6 mmol) followed by a slow addition of a solution of sulfur trioxide pyridine complex (1.28 g, 8.02 mmol) in anhydrous DMSO (12 mL). The reaction mixture was stirred for 30 min and cold water (70 mL) was slowly added. The above content was acidified with 3 N HCl to pH 2.5, extracted twice with EtOAc, washed with brine, dried over MgSO4, and concentrated to yield the title compound as a light brown solid. Retention time=1.22 min (Method A); MS (M−H)−=407.

Aufarbeitung

  1. extractionextracted twice with EtOAc
  2. washwashed with brine
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-23016b81fa0b43678f342aa48249d70f
Quelldatensatz
uspto-grants-2012_08
Patentnummer
US08252820B2

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