Reaktion #216228

ord-e9f3eb7da128481f975bd89182c9bd1c

Reaktionsgleichung

O=C([O-])C(Br)Cc1ccccc1
benzylbromoacetate
CC(C)c1cc(O)cc2c1C(=O)N(CSc1ccccc1)S2(=O)=O
4-isopropyl-6-hydroxy-2-phenylthiomethyl-saccharin
O=C([O-])[O-].[K+].[K+]
K2CO3
CC(C)=O
acetone
→
CC(C)c1cc(OCC(=O)OCc2ccccc2)cc2c1C(=O)N(CSc1ccccc1)S2(=O)=O
4-isopropyl-6-(benzyloxycarbonylmethoxy)-2-phenylthiomethylsaccharin

Edukte

O=C([O-])C(Br)Cc1ccccc1
benzylbromoacetate
CC(C)c1cc(O)cc2c1C(=O)N(CSc1ccccc1)S2(=O)=O
4-isopropyl-6-hydroxy-2-phenylthiomethyl-saccharin
O=C([O-])[O-].[K+].[K+]
K2CO3
CC(C)=O
acetone

Reagenzien

Keine

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    workup.STIRRINGThe mixture was stirred for 6 hours
  2. 2
    Filtrationfiltered
  3. 3
    Einengenthe filtrate was concentrated in vacuo
  4. 4
    SonstigeThe residue was purified by medium pressure chromatography
  5. 5
    Wascheneluting with 20% ethyl acetate/hexane

Vorschrift

A mixture of 4-isopropyl-6-hydroxy-2-phenylthiomethyl-saccharin (3.5 g, 9.63 mmol), acetone (25 mL) and K2CO3 (2.66 g, 19.26 mmol) was stirred under nitrogen for 2 minutes, then benzylbromoacetate (2.4 mL, 14.45 mmol) was added. The mixture was stirred for 6 hours, filtered, and the filtrate was concentrated in vacuo. The residue was purified by medium pressure chromatography eluting with 20% ethyl acetate/hexane to afford 4.67 (100%) of 4-isopropyl-6-(benzyloxycarbonylmethoxy)-2-phenylthiomethylsaccharin.

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US05466701uspto-grants-1995_11