Reaktion #45253

ord-59cb70e321af4807b0cad051bb2f1012

Reaktionsgleichung

CO
methanol
c1ccc(P(c2ccccc2)c2ccccc2)cc1
triphenylphosphine
CCCCOC(=O)NS(=O)(=O)NCC(=O)OCC
ethyl 2-((N-(butyloxycarbonyl)sulfamoyl)amino)acetate
CC(C)OC(=O)/N=N/C(=O)OC(C)C
DIAD
→
CCCCOC(=O)N(C)S(=O)(=O)NCC(=O)OCC
ethyl 2-((N-(butyloxycarbonyl)-N-methylsulfamoyl)amino)acetate

Edukte

CO
methanol
c1ccc(P(c2ccccc2)c2ccccc2)cc1
triphenylphosphine
CCCCOC(=O)NS(=O)(=O)NCC(=O)OCC
ethyl 2-((N-(butyloxycarbonyl)sulfamoyl)amino)acetate
CC(C)OC(=O)/N=N/C(=O)OC(C)C
DIAD

Reagenzien

Keine

Lösungsmittel

C1CCOC1
THF
C1CCOC1
THF

Reaktionsbedingungen

Temperatur
0°CELSIUS
Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    Temperaturwarmed to RT
  2. 2
    workup.STIRRINGis stirred overnight
  3. 3
    SonstigeAfter the solvent is removed in vacuo
  4. 4
    Sonstigethe residue is purified by column chromatography

Vorschrift

To a solution of methanol (8.5 mmol) and triphenylphosphine (2.6 g, 8.5 mol) in dry THF is added a solution of ethyl 2-((N-(butyloxycarbonyl)sulfamoyl)amino)acetate from the previous step (2.4 g, 8.5 mol) and DIAD (2.0 g, 8.5 mmol) in dry THF dropwise at 0° C. under N2 atmosphere. The mixture is stirred at 0° C. for 2 h, warmed to RT and is stirred overnight. After the solvent is removed in vacuo, the residue is purified by column chromatography to afford ethyl 2-((N-(butyloxycarbonyl)-N-methylsulfamoyl)amino)acetate.

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US07737283B2uspto-grants-2010_06