Reaktion #588441

ord-0f1cd03a71454867b1d480444d3ac576

Reaktionsgleichung

CCOC(C)=O
EA
O=S1(=O)NCCN1C1CC1
2-cyclopropyl-[1,2,5]thiadiazolidine 1,1-dioxide
COC(=O)c1cc(S(C)(=O)=O)c(F)cc1C
methyl 4-fluoro-5-methanesulfonyl-2-methylbenzoate
O=C([O-])[O-].[Cs+].[Cs+]
Cs2CO3
→
COC(=O)c1cc(S(C)(=O)=O)c(N2CCN(C3CC3)S2(=O)=O)cc1C
amorphous solid
Ausbeute 47.3%
COC(=O)c1cc(S(C)(=O)=O)c(N2CCN(C3CC3)S2(=O)=O)cc1C
Methyl 4-(5-cyclopropyl-1,1-dioxo-[1,2,5]thiadiazolidin-2-yl)-5-methanesulfonyl-2-methylbenzoate
Ausbeute 47.3%

Edukte

CCOC(C)=O
EA
O=S1(=O)NCCN1C1CC1
2-cyclopropyl-[1,2,5]thiadiazolidine 1,1-dioxide
COC(=O)c1cc(S(C)(=O)=O)c(F)cc1C
methyl 4-fluoro-5-methanesulfonyl-2-methylbenzoate
O=C([O-])[O-].[Cs+].[Cs+]
Cs2CO3

Reagenzien

Keine

Lösungsmittel

CN(C)C=O
DMF

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    Waschenwashing 3 times with 20 ml of water each time
  2. 2
    TrocknenAfter drying over Na2SO4
  3. 3
    Sonstigethe solvent was removed in vacuo

Vorschrift

203 mg of 2-cyclopropyl-[1,2,5]thiadiazolidine 1,1-dioxide, 308 mg of methyl 4-fluoro-5-methanesulfonyl-2-methylbenzoate and 2.44 g of Cs2CO3 were stirred in 25 ml of anhydrous DMF at 80° C. for 5 hours. Standing at RT for 2 days was followed by dilution with 200 ml of EA and washing 3 times with 20 ml of water each time. After drying over Na2SO4, the solvent was removed in vacuo. Chromatography on silica gel with DIP afforded 230 mg of an amorphous solid.

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US07772262B2uspto-grants-2010_08