158257-34-2

Basic information

• Product Name: 1H-Pyrrole-1-carboxylic acid, 2,5-dihydro-3-hydroxy-5-oxo-2-(phenylmethyl)-, phenylmethyl ester, (2S)-
• CAS NO: 158257-34-2
• Molecular Formula: C19H17NO4
• Molecular Weight: 323.348
• Mol File: 158257-34-2.mol
• Article Data: 4

Chemical Properties

• CAS DataBase Reference: 1H-Pyrrole-1-carboxylic acid, 2,5-dihydro-3-hydroxy-5-oxo-2-(phenylmethyl)-, phenylmethyl ester, (2S)-(CAS DataBase Reference)
• NIST Chemistry Reference: 1H-Pyrrole-1-carboxylic acid, 2,5-dihydro-3-hydroxy-5-oxo-2-(phenylmethyl)-, phenylmethyl ester, (2S)-(158257-34-2)
• EPA Substance Registry System: 1H-Pyrrole-1-carboxylic acid, 2,5-dihydro-3-hydroxy-5-oxo-2-(phenylmethyl)-, phenylmethyl ester, (2S)-(158257-34-2)

Safety Data

• Hazardous Substances Data: 158257-34-2(Hazardous Substances Data)

Upstream product

• 25613-60-9 Nα-carbobenzyloxy-L-phenylalanine N-carboxanhydride 
• 1161-13-3 N-Cbz-L-Phe 
• 55740-07-3 (4S)-4-benzyl-5-oxo-1,3-oxazolidine-3-carboxylic acid benzyl ester 
• 220931-41-9 (S)-4-Benzyl-5-[1-ethoxycarbonyl-meth-(E)-ylidene]-oxazolidine-3-carboxylic acid benzyl ester 

Relevant articles and documents

Synthesis of N-substituted 3-ammomethylidenetetramic acids

(S)-3-(Dimethylamino)methylidene-5-benzyltetramic acid derivatives 4a and 4b were prepared in three steps from N-protected (S)-3-phenylalanines 1a and 1b, respectively. Similarly, N-[N-(benzyloxycarbonyl)glycyl]grycine (1c) was transformed into the enamitione 4c. Acid-catalysed coupling of enaminones 4a-c with aliphatic, aromatic, and heteroaromatic primary amines 5-34 afforded the corresponding N(3′)-substituted 3-aminomethylidenetetramic acid derivatives 35-64 in 29-96% yields. Georg Thieme Verlag Stuttgart.

An improved procedure to homochiral cyclic statines

Chiral tetramic acids were prepared in high yields by the reaction of N-protected amino acids with Meldrum's acid employing DCC as a carboxyl activating agent. Reduction or hydrogenation of these tetramic acids produced homochiral cyclic statines.