9-Fluorenylmethyl chloroformate → 5-{[(9h-Fluoren-9-ylmethoxy)carbonyl]amino}-2,4-dimethylbenzenesulfonic acid

HRID 1802460Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1802460
[Na+].[NH2:2][C:3]1[C:4]([CH3:14])=[CH:5][C:6]([CH3:13])=[C:7]([S:9]([O-:12])(=[O:11])=[O:10])[CH:8]=1.C([O-])(O)=O.[Na+].Cl[C:21]([O:23][CH2:24][CH:25]1[C:37]2[CH:36]=[CH:35][CH:34]=[CH:33][C:32]=2[C:31]2[C:26]1=[CH:27][CH:28]=[CH:29][CH:30]=2)=[O:22]>O1CCOCC1.O>[CH:36]1[C:37]2[CH:25]([CH2:24][O:23][C:21]([NH:2][C:3]3[C:4]([CH3:14])=[CH:5][C:6]([CH3:13])=[C:7]([S:9]([OH:12])(=[O:10])=[O:11])[CH:8]=3)=[O:22])[C:26]3[C:31](=[CH:30][CH:29]=[CH:28][CH:27]=3)[C:32]=2[CH:33]=[CH:34][CH:35]=1

Komponenten

6

Edukt 3

HCID 343679-Fluorenylmethyl chloroformateHCID 516892Sodium BicarbonateHCID 23691697Sodium 5-amino-2,4-dimethylbenzene-1-sulfonate

Produkt 1

HCID 594360375-{[(9h-Fluoren-9-ylmethoxy)carbonyl]amino}-2,4-dimethylbenzenesulfonic acid

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

To a solution of 5-amino-2,4-dimethylbenzenesulfonic acid sodium salt (3.0 g, 13.4 mmol) in dioxane (37 mL) and water (37 ml) was added NaHCO3 (2.5 g, 29.6 mmol) and 9-fluoreneylmethyl chloroformate. The mixture was then stirred at room temperature overnight and then quenched with 1N HCl and extracted with EtOAc. The organic layers were concentrated in vacuo. Purification by silica gel chromatography (0-10% MeOH/DCM) resulted in the title compound.

Aufarbeitung

  1. customquenched with 1N HCl
  2. extractionextracted with EtOAc
  3. concentrationThe organic layers were concentrated in vacuo
  4. customPurification by silica gel chromatography (0-10% MeOH/DCM)

Quellen und Nachweise

ORD-Eintrag
ord-bbd3401ec28f4774b4dbb717bfe4205d
Quelldatensatz
uspto-grants-2013_01
Patentnummer
US08349865B2

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