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US 7,064,214 B2Granted
Methods of preparing sulfinamides and sulfoxides
AssigneeApsinterm LLC
InventorsChris Hugh Senanayake, Zhengxu Han, Dhileepkumar Krishnamurthy, Derek Pflum, Harold Scott Wilkinson
Life of this patent
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Abstract
This invention encompasses novel methods of preparing sulfinamides and sulfoxides, particularly stereomerically pure sulfinamides and sulfoxides. The invention further encompasses novel compounds from which sulfinamides and sulfoxides can be prepared.
Claims28
A method of preparing a sulfinamide or sulfoxide of Formula 2:
- which comprises contacting a compound of Formula 1:
- wherein n is 0 to 3;
- L is COmR3 or SOmR3, wherein m is 0 to 3;
- R1 and R2 together form a cyclic structure or each of R1 and R2 is independently substituted or unsubstituted alkyl, substituted or unsubstituted aralkyl, substituted or unsubstituted heteroalkyl, substituted or unsubstituted aryl, substituted or unsubstituted heterocycle;
- R1′ and R2′ together form a cyclic structure or each of R1′ and R2′ is independently hydrogen, substituted or unsubstituted alkyl, substituted or unsubstituted aralkyl, substituted or unsubstituted heteroalkyl, substituted or unsubstituted aryl, or substituted or unsubstituted heterocycle;
- Ra and Rb together form a cyclic structure or each of Ra and Rb is independently hydrogen, substituted or unsubstituted alkyl, substituted or unsubstituted aralkyl, substituted or unsubstituted heteroalkyl, substituted or unsubstituted aryl, or substituted or unsubstituted heterocycle;
- and each of R3 and X is independently a polymer bound alkyl, aryl or heteroalkyl, substituted or unsubstituted alkyl, substituted or unsubstituted aralkyl, substituted or unsubstituted heteroalkyl, substituted or unsubstituted aryl, substituted or unsubstituted ether, substituted or unsubstituted ester, substituted or unsubstituted ketone, substituted or unsubstituted phosphonate, substituted or unsubstituted phosphonic acid ester, substituted or unsubstituted phosphinoyl, substituted or unsubstituted sulfide, substituted or unsubstituted sulfone, substituted or unsubstituted sulfinyl imine, substituted or unsubstituted heterocycle, or —NR4R5, wherein R4 and R5 together with the nitrogen atom to which they are attached form a heterocycle or each of R4 and R5 is independently hydrogen, substituted or unsubstituted alkyl, substituted or unsubstituted heteroalkyl, substituted or unsubstituted aralkyl, substituted or unsubstituted aryl, substituted or unsubstituted ether, substituted or unsubstituted sulfide, or substituted or unsubstituted heterocycle;
- with a compound of formula MY, wherein M is a metal or metal complex capable of transferring Y to the positively charged sulfur atom of the compound of Formula 1 and Y is independently substituted or unsubstituted alkyl, substituted or unsubstituted aralkyl, substituted or unsubstituted heteroalkyl, substituted or unsubstituted aryl, substituted or unsubstituted ether, substituted or unsubstituted ester, substituted or unsubstituted ketone, substituted or unsubstituted phosphonate, substituted or unsubstituted phosphonic acid ester, substituted or unsubstituted phosphinoyl, substituted or unsubstituted sulfide, substituted or unsubstituted sulfone, substituted or unsubstituted sulfinyl imine, substituted or unsubstituted heterocycle, or is of the formula —NR6R7, wherein R6 and R7 together with the nitrogen atom to which they are attached form a heterocycle or each of R6 and R7 is independently a polymer bound alkyl, aryl or heteroalkyl;
- hydrogen;
- substituted or unsubstituted alkyl;
- substituted or unsubstituted aralkyl;
- substituted or unsubstituted heteroalkyl;
- substituted or unsubstituted aryl;
- substituted or unsubstituted ether;
- substituted or unsubstituted ester;
- substituted or unsubstituted ketone;
- substituted or unsubstituted phosphonate;
- substituted or unsubstituted phosphonic acid ester;
- substituted or unsubstituted phosphinoyl;
- substituted or unsubstituted sulfide;
- substituted or unsubstituted sulfone;
- substituted or unsubstituted sulfinyl imine;
- substituted or unsubstituted heterocycle;
- under conditions suitable for the formation of the compound of Formula 2:
21 more elements
Dependencies are inferred from the claim text.