168034-55-7

Basic information

• Product Name: 3-Pyrrolidineaceticacid,5-carboxy-,(3R-cis)-(9CI)
• Synonyms: 3-Pyrrolidineaceticacid,5-carboxy-,(3R-cis)-(9CI)
• CAS NO: 168034-55-7
• Molecular Formula: C7H11NO4
• Molecular Weight: 173.17
• Product Categories: PYRROLE
• Mol File: 168034-55-7.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 3-Pyrrolidineaceticacid,5-carboxy-,(3R-cis)-(9CI)(CAS DataBase Reference)
• NIST Chemistry Reference: 3-Pyrrolidineaceticacid,5-carboxy-,(3R-cis)-(9CI)(168034-55-7)
• EPA Substance Registry System: 3-Pyrrolidineaceticacid,5-carboxy-,(3R-cis)-(9CI)(168034-55-7)

Safety Data

• Hazardous Substances Data: 168034-55-7(Hazardous Substances Data)

Upstream product

• 40216-83-9 L-4-hydroxyproline methyl ester hydrochloride 
• 51-35-4 4R-4-hydroxyproline 
• 148587-50-2 (2S,4S)-4-tert-Butoxycarbonylmethyl-5-oxo-pyrrolidine-1,2-dicarboxylic acid 2-benzyl ester 1-methyl ester 
• 146356-00-5 N-methoxycarbonyl (S)-pyroglutamic acid benzylester 
• 168034-40-0 diethyl 1-benzyloxycarbonyl-4-<(ethoxycarbonyl)methyl>pyrrolidine-2,2-dicarboxylate 
• 168034-39-7 diethyl 4-<(ethoxycarbonyl)methyl>pyrrolidine-2,2-dicarboxylate 
• 156452-92-5 diethyl N-benzyloxycarbonyl-5-hydroxypyrrolidine-2,2-dicarboxylate 
• 156452-93-6 diethyl N-benzyloxycarbonyl-2,3-dihydropyrrole-2,2-dicarboxylate 
• 16217-15-5 1-benzyloxycarbonyl-4-oxo-L-proline methyl ester 
• 117653-35-7 2-methyl-1-(phenylmethyl) 4-<2-(1,1-dimethylethoxy)-2-oxoethylidene>-1,2-pyrrolidinedicarboxylate 
• 102195-80-2 (S)-1-tert-butyl 2-methyl 4-oxopyrrolidine-1,2-dicarboxylate 
• 74844-91-0 1-tert-butyl 2-methyl (2S,4R)-4-hydroxy-1,2-pyrrolidinedicarboxylate 
• 327989-71-9 (E)-N^α-(1,1-dimethylethoxycarbonyl)-4-(2-cyanomethylene)-L-proline methyl ester 
• 327989-70-8 N^α-(1,1-dimethylethoxycarbonyl)-trans-4-(2-cyanomethyl)-L-proline methyl ester 

Relevant articles and documents

Facile syntheses of conformationally constrained analogues of lysine and homoglutamic acid

A facile divergent synthesis of the novel amino acid trans-4-aminoethyl-l- proline and trans-4-carboxymethyl-l-proline from commercially available trans-4-hydroxy-l-proline was developed. These conformationally constrained analogues of l-lysine and l-homoglutamic acid are useful proline templated amino acids (PTAAs) with potential applications in protein engineering and de novo protein design.

Synthesis of all four diastereoisomers of 4-(carboxymethyl)proline, a conformationally constrained analogue of 2-aminoadipic acid

The dirhodium(II) tetraacetate catalysed reaction of ethyl diazoacetate with 2,3-dihydropyrrole-2,2-dicarboxylate 5 afforded the useful 2-azabicyclohexane 6.Its conversion into the proline-γ-acetic acid equivalent 9 as well as into the four isomers constituting the 4-(carboxymethyl)proline 13 (16a-19a) whose absolute configuration was established by an alternative asymmetric synthesis of two of them is described.Preliminary data concerning the affinity of compounds 16a-19a for the NMDA site of the NMDA receptor complex are also reported.

Synthesis of (2S,4S)-2-Carboxy-4-Pyrrolidine Acetic Acid, a Conformationally Constrained 2-Amino Adipic Acid Analogue

(2S,4S)-2-carboxy-4-pyrrolidine acetic acid was synthesized from (S)-pyroglutamic acid in 26 percent overall yield by a regiospecific deprotonation of the N-methoxycarbonyl benzylester 4. Key Words: pyroglutamic acid, excitatory amino-acids, alkyl bromoacetate, sodium cyanoborohydride.