103322-13-0

Basic information

• Product Name: 1H-Pyrrole-2-carboxylicacid,1-(chlorocarbonyl)-2,3-dihydro-,methylester,(S)-(9CI)
• Synonyms: 1H-Pyrrole-2-carboxylicacid,1-(chlorocarbonyl)-2,3-dihydro-,methylester,(S)-(9CI)
• CAS NO: 103322-13-0
• Molecular Formula: C₇H₈ClNO₃
• Molecular Weight: 189.6
• Product Categories: ACIDHALIDE
• Mol File: 103322-13-0.mol
• Article Data: 1

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 1H-Pyrrole-2-carboxylicacid,1-(chlorocarbonyl)-2,3-dihydro-,methylester,(S)-(9CI)(CAS DataBase Reference)
• NIST Chemistry Reference: 1H-Pyrrole-2-carboxylicacid,1-(chlorocarbonyl)-2,3-dihydro-,methylester,(S)-(9CI)(103322-13-0)
• EPA Substance Registry System: 1H-Pyrrole-2-carboxylicacid,1-(chlorocarbonyl)-2,3-dihydro-,methylester,(S)-(9CI)(103322-13-0)

Safety Data

• Hazardous Substances Data: 103322-13-0(Hazardous Substances Data)

Upstream product

• 75-44-5 phosgene 
• 4931-66-2 methyl (S)-pyroglutamate 
• 98-79-3 L-Pyroglutamic acid 

Downstream Products

• 85665-59-4 (S)-methyl 1-(chlorocarbonyl)pyrrolidine-2-carboxylate 
• 147-85-3 L-proline 

Relevant articles and documents

Amino Acids. 7. A Novel Synthetic Route to L-Proline

Reaction of L-5-oxoproline esters L-2 with phosgene at 0 deg C gives L-5,5-dichloro-1-(chlorocarbonyl)proline esters L-6, which readily lose hydrogen chloride to form L-5-chloro-1-(chlorocarbonyl)-4,5-dehydroproline esters L-7.Catalytic hydrogenation (Pd/C, 180 bar) of L-7 yields L-1-(chlorocarbonyl)proline esters L-15 and thence, upon hydrolysis, L-proline (L-17).A 'one-pot reaction' for the whole sequence is described, starting from easily accessible L-5-oxoproline esters and yielding L-proline in 78percent overall yield and 99.7percent optical purity.