529486-21-3

Basic information

• Product Name: (2S,1'S)-pyrrolidine-2-carboxylic acid (1-benzyl-2-hydroxyethyl)amide
• Synonyms: (2S,1'S)-pyrrolidine-2-carboxylic acid (1-benzyl-2-hydroxyethyl)amide
• CAS NO: 529486-21-3
• Molecular Weight: 248.325
• Mol File: 529486-21-3.mol
• Article Data: 5

Chemical Properties

• CAS DataBase Reference: (2S,1'S)-pyrrolidine-2-carboxylic acid (1-benzyl-2-hydroxyethyl)amide(CAS DataBase Reference)
• NIST Chemistry Reference: (2S,1'S)-pyrrolidine-2-carboxylic acid (1-benzyl-2-hydroxyethyl)amide(529486-21-3)
• EPA Substance Registry System: (2S,1'S)-pyrrolidine-2-carboxylic acid (1-benzyl-2-hydroxyethyl)amide(529486-21-3)

Safety Data

• Hazardous Substances Data: 529486-21-3(Hazardous Substances Data)

Upstream product

• 169515-57-5 (S)-tert-butyl 2-((S)-1-hydroxy-3-phenylpropan-2-ylcarbamoyl)pyrrolidine-1-carboxylate 
• 88084-14-4 benzyl 2-[(1-benzyl-2-hydroxyethyl)carbamoyl]pyrrolidine-1-carboxylate 
• 3182-95-4 L-Phenylalaninol 
• 1148-11-4 N-Benzyloxycarbonyl-L-proline 
• 15761-39-4 1-(tert-butoxycarbonyl)-L-proline 
• 147-85-3 L-proline 

Downstream Products

• 324764-12-7 {2-[(S)-2-((S)-1-Hydroxymethyl-2-phenyl-ethylcarbamoyl)-pyrrolidin-1-yl]-1,1-dimethyl-2-oxo-ethyl}-carbamic acid 9H-fluoren-9-ylmethyl ester 
• 324764-16-1 C₆₀H₈₂N₈O₁₂ 
• 193007-24-8 C₅₂H₆₆N₈O₁₂ 
• 324764-15-0 {1-[2-(4-tert-butoxy-2-{2-[2-(1-hydroxymethyl-2-phenyl-ethylcarbamoyl)-pyrrolidin-1-yl]-1,1-dimethyl-2-oxo-ethylcarbamoyl}-pyrrolidin-1-yl)-1,1-dimethyl-2-oxo-ethylcarbamoyl]-3-carbamoyl-propyl}-carbamic acid 9H-fluoren-9-ylmethyl ester 
• 193007-44-2 2-[(4-hydroxy-pyrrolidine-2-carbonyl)-amino]-pentanedioic acid 5-amide 1-{[2-(4-hydroxy-2-{2-[2-(1-hydroxymethyl-2-phenyl-ethylcarbamoyl)-pyrrolidin-1-yl]-1,1-dimethyl-2-oxo-ethylcarbamoyl}-pyrrolidin-1-yl)-1,1-dimethyl-2-oxo-ethyl]-amide} 
• 324764-14-9 [2-((2S,4R)-4-tert-Butoxy-2-{2-[(S)-2-((S)-1-hydroxymethyl-2-phenyl-ethylcarbamoyl)-pyrrolidin-1-yl]-1,1-dimethyl-2-oxo-ethylcarbamoyl}-pyrrolidin-1-yl)-1,1-dimethyl-2-oxo-ethyl]-carbamic acid 9H-fluoren-9-ylmethyl ester 
• 324764-13-8 (2S,4R)-4-tert-Butoxy-2-{2-[(S)-2-((S)-1-hydroxymethyl-2-phenyl-ethylcarbamoyl)-pyrrolidin-1-yl]-1,1-dimethyl-2-oxo-ethylcarbamoyl}-pyrrolidine-1-carboxylic acid 9H-fluoren-9-ylmethyl ester 

Relevant articles and documents

Synthesis and characterization of new chiral azolinium salts, precursors to N-heterocyclic carbenes, derived from l-proline

A short and flexible procedure for the preparation of seven chiral azolinium and five functionalized chiral azolinium salts, precursors to N-heterocyclic carbenes, derived from l-proline has been developed. Moderate to good overall yields were obtained. Some NHC dimers and thiones were isolated. X-ray crystal structure determinations of two [Rh-NHC] complexes were also reported.

Attempts toward the synthesis of the peptaibol antiamoebin by using the 'azirine/oxazolone method'

The two segments, 1-9 and 10-16, of the peptaibol antibiotic antiamoebin I, i.e., the nonapeptide Ac-Phe-Aib-Aib-Aib-D,L-Iva-Gly-Leu-Aib-Aib-OH (15) and the heptapeptide Z-Hyp-Gln-D,L-Iva-Hyp-Aib-Pro-Pheol (34), have been prepared as mixtures of the epimers containing D,L-Iva. All α,α-disubstituted α-amino acids were introduced by the 'azirine/oxazolone method', in which amino or peptide acids are coupled with the corresponding 2H-azirin-3-amines, followed by selective hydrolysis of the terminal amide bond. The amino acids Hyp and Gln were introduced as Z-protected4) (2S,4R)-4-(tert-butoxy) proline (19) and methyl N-[bis(4-methoxyphenyl)methyl]glutamine (26). Coupling of peptide segments was achieved via the 'mixed anhydride' method, the DCC/HOBt or TBTU/HOBt strategy. The crystal structure of the segment 6-9 was determined by X-ray crystallography and displayed the presence of a β-turn conformation. Copyright

Chemical synthesis of 15N-labeled analogues of zervamicin IIB

Analogues of 16-membered peptide antibiotic zervamicin IIB with the Gln3 and Gln11 residues 15N-labeled at the Cα-atoms were synthesized by coupling the antibiotic segments (1-4), (5-9), and (10-16). In turn, these were prepared by a stepwise chain elongation in solution starting from their C-termini using benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphate (BOP) as an activating agent. The sterically hindered 2-aminoisobutyric acid was introduced by the BOP-dimethylaminopyridine system with the preactivation of the carboxyl component. The segment condensation was performed with the use of the 6-trifluoromethylbenzotriazol-1-yloxy-tris(pyrrolidino)phosphonium hexafluorophosphate activating reagent. The homogeneity of the resulting zervamicin analogues was confirmed by HPLC, and their structures were proved by NMR spectroscopy and FAB mass spectrometry.