Patent ID: 6420573
Filing Date: 2002-07-16
Classification: C07C,C07D

Abstract:
A process for producing a compound of the formula:â€ƒYâ€”C(&boxH;O)â€”C(R1)(R2)â€”CH2â€”S(O)nR3â€ƒâ€ƒIwherein:Y is hydroxy or XONXâ€”, where each X is independently hydrogen, lower alkyl or lower acyl; R1 is hydrogen or lower alkyl; R2 is hydrogen, lower alkyl, aryl, aralkyl, cycloalkyl, cycloalkylalkyl, or R1 and R2 together with the carbon atom to which they are attached form a cycloalkyl or heterocyclo group; R3 is aryl or â€”Ar1â€”Aâ€”Ar2, where each of Ar1 and Ar2 is independently an optionally substituted phenyl, and A is a bond, â€”CH2â€” or â€”Oâ€”; and n is 0, 1 or 2; said process comprising:alkylating a compound of the formula: ROâ€”C(&boxH;O)â€”CH(R1 )(R2)â€ƒâ€ƒII wherein R is alkyl or hydrogen, with an arylmethylthio compound of the formula:R3SCH2â€”Zâ€ƒâ€ƒIII wherein Z is a leaving group, to produce a thioether compound of the formula:ROâ€”C(&boxH;O)â€”C(R1)(R2)â€”CH2SR3â€ƒâ€ƒIVA and optionally(i) modifying the acyl substituent by contacting the thioether compound of Formula IVA with a compound of the formula YH to produce a compound of the formula: Yâ€”C(&boxH;O)â€”C(R1)(R2)â€”CH2SR3â€ƒâ€ƒVA and when n=1 or 2 (ii) oxidizing the sulfur atom by contacting the compound of Formula VA with an oxidizing agent to produce the compound of Formula I; or (i) oxidizing the sulfur atom by contacting the thioether compound of Formula IVA with an oxidizing agent to produce a compound of the formula: ROâ€”C(&boxH;O)â€”C(R1)(R2)â€”CH2â€”S(O)nR3â€ƒâ€ƒVIA where n=1 or 2, and optionally (ii) modifying the acyl substituent by contacting the compound of Formula VIA with YH to produce the compound of Formula I.