212568-27-9

Basic information

• Product Name: (R)-2-Chloro-propionic acid (S)-4,4-dimethyl-2-oxo-1-phenyl-pyrrolidin-3-yl ester
• Synonyms: (R)-2-Chloro-propionic acid (S)-4,4-dimethyl-2-oxo-1-phenyl-pyrrolidin-3-yl ester
• CAS NO: 212568-27-9
• Molecular Weight: 295.766
• Mol File: 212568-27-9.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: (R)-2-Chloro-propionic acid (S)-4,4-dimethyl-2-oxo-1-phenyl-pyrrolidin-3-yl ester(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-2-Chloro-propionic acid (S)-4,4-dimethyl-2-oxo-1-phenyl-pyrrolidin-3-yl ester(212568-27-9)
• EPA Substance Registry System: (R)-2-Chloro-propionic acid (S)-4,4-dimethyl-2-oxo-1-phenyl-pyrrolidin-3-yl ester(212568-27-9)

Safety Data

• Hazardous Substances Data: 212568-27-9(Hazardous Substances Data)

Upstream product

• 7623-09-8 2-chloropropionyl chloride 
• 169221-12-9 (S)-3-hydroxy-4,4-dimethyl-1-phenyl-2-pyrrolidinone 

Downstream Products

• 7474-05-7 (R)-2-chloropropionic acid 

Relevant articles and documents

(R)- and (S)-3-hydroxy-4,4-dimethyl-1-phenyl-2-pyrrolidinone as chiral auxiliaries in the enantioselective preparation of α-aryloxypropanoic acid herbicides and α-chlorocarboxylic acids

rac-α-Chlorocarboxylic acids, rac-9a-e, were formally deracemized by reaction of the corresponding acyl chlorides with the chiral auxiliaries (R)- and (S)-3-hydroxy-4,4-dimethyl-1-phenyl-2-pyrrolidinone, (R)- and (S)-4, followed by mild alkaline hydrolysis. The highest o.p. (99%) was obtained in the case of (S)-α-chloropropanoic acid, a known precursor for the synthesis of (R)-α-aryloxypropanoic acid herbicides such as dichlorprop-P, (R)-3a, or mecoprop-P, (R)-3b, which, together with their enantiomers, were also obtained in moderate e.e.s by dynamic kinetic resolution from (αRS,3S)-4,4- dimethyl-2-oxo-l-phenylpyrrolidin-3-yl α-bromopropanoate, (αRS,3S)-6, by reaction with the corresponding phenoxide followed by mild acid hydrolysis.