Synthesis of [ 13 C] and [ 2 H] substituted methacrylic...

Details Synthesis of [ 13 C] and [ 2 H] substituted methacrylic... Synthesis of [ 13 C] and [ 2 H] substituted methacrylic...

2008-01-22

2008-01-22

Eyler, Yvonne (Department: 1621)

Organic compounds -- part of the class 532-570 series

Organic compounds

Carboxylic acid esters

C560S015000, C424S001810

Reexamination Certificate

active

07321049

ABSTRACT:
The present invention is directed to labeled compounds of the formulaewherein Q is selected from the group consisting of —S—, —S(═O)—, and —S(═O)2—, Z is selected from the group consisting of 1-naphthyl, substituted 1-naphthyl, 2-naphthyl, substituted 2-naphthyl, and phenyl groups with the structurewherein R1, R2, R3, R4and R5are each independently selected from the group consisting of hydrogen, a C1-C4lower alkyl, a halogen, and an amino group selected from the group consisting of NH2, NHR and NRR′ where R and R′ are each independently selected from the group consisting of a C1-C4lower alkyl, an aryl, and an alkoxy group, and X is selected from the group consisting of hydrogen, a C1-C4lower alkyl group, and a fully-deuterated C1-C4lower alkyl group. The present invention is also directed to a process of preparing labeled compounds, e.g., process of preparing [13C]methacrylic acid by reacting a (CH3CH2O—13C(O)—13CH2)— aryl sulfone precursor with13CHI to form a (CH3CH2O—13C(O)—13C(13CH3)2)— aryl sulfone intermediate, and, reacting the (CH3CH2O—13C(O)—13C(13CH3)2)— aryl sulfone intermediate with sodium hydroxide, followed by acid to form [13C]methacrylic acid. The present invention is further directed to a process of preparing [2H8]methyl methacrylate by reacting a (HOOC—C(C2H3)2— aryl sulfinyl intermediate with CD3I to form a (2H3COOC—C(C2H3)2)— aryl sulfinyl intermediate, and heating the(2H3COOC—C(C2H3)2)— aryl sulfinyl intermediate at temperatures and for time sufficient to form [2H8]methyl methacrylate.

REFERENCES:
Domenico Spinelli, Paolo Zanirato, and Elvira Di Miceli J. Org. Chem. 1997, 62,4921-4923.
Douglass F. Taber, Yanong Wang Journal of Labelled Compounds and Radiopharmaceuticals vol. 36, Issue 7, pp. 655-660, 1995 (please see the enclosed abstract).

Affiliated with

Also associated with

Rating

Synthesis of [ 13 C] and [ 2 H] substituted methacrylic... does not yet have a rating. At this time, there are no reviews or comments for this patent.

If you have personal experience with Synthesis of [ 13 C] and [ 2 H] substituted methacrylic..., we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Synthesis of [ 13 C] and [ 2 H] substituted methacrylic... will most certainly appreciate the feedback.

Rate now

Comments { 0 }

Profile ID: LFUS-PAI-O-2811683