Conversion of carbamates to amidosulfones and amides. Synthesis of the [14C]-labeled antiobesity agent Ro23-7637.
[reaction: see text] Carbamates of primary and secondary amines react with the dianion of methyl phenyl sulfone to yield amidosulfones. Alylation of the amidosulfone followed by reductive removal of the sulfonyl residue gives an amide.
White
James D
JD
Department of Chemistry, Oregon State University, Corvallis 97331-4003, USA. james.white@orst.edu
Blakemore
Paul R
PR
Milicevic
Selena
S
Choudhry
Satish C
SC
Cupano
Joseph
J
Serico
Lucia
L
D000478:Alkylation; D000577:Amides / Q000737:chemistry; D019440:Anti-Obesity Agents / Q000138:chemical synthesis*; D002219:Carbamates / Q000138:chemical synthesis*; D002250:Carbon Radioisotopes / Q000737:chemistry; D007202:Indicators and Reagents; D007553:Isotope Labeling; D010880:Piperidines / Q000138:chemical synthesis*; D011725:Pyridines / Q000138:chemical synthesis*; D019275:Radiopharmaceuticals / Q000138:chemical synthesis; D013450:Sulfones / Q000737:chemistry
D000577:Amides; D019440:Anti-Obesity Agents; D002219:Carbamates; D002250:Carbon Radioisotopes; D007202:Indicators and Reagents; D010880:Piperidines; D011725:Pyridines; D019275:Radiopharmaceuticals; D013450:Sulfones; C083287:Ro 23-7637