142114-82-7

Basic information

• Product Name: L-Proline, 1-(2-azidobenzoyl)-, methyl ester
• CAS NO: 142114-82-7
• Molecular Formula: C13H14N4O3
• Molecular Weight: 274.279
• Mol File: 142114-82-7.mol
• Article Data: 7

Chemical Properties

• CAS DataBase Reference: L-Proline, 1-(2-azidobenzoyl)-, methyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: L-Proline, 1-(2-azidobenzoyl)-, methyl ester(142114-82-7)
• EPA Substance Registry System: L-Proline, 1-(2-azidobenzoyl)-, methyl ester(142114-82-7)

Safety Data

• Hazardous Substances Data: 142114-82-7(Hazardous Substances Data)

Upstream product

• 67-56-1 methanol 
• 166451-14-5 (2S)-1-(2-azido-benzoyl)-pyrrolidine-2-carboxylic acid 
• 31162-13-7 2-azidobenzoic acid 
• 118-92-3 anthranilic acid 
• 610-14-0 2-nitrobenzyl chloride 
• 2133-40-6 L-proline methyl ester monohydrochloride 
• 2577-48-2 methyl (2S)-pyrrolidine carboxylate 
• 34897-85-3 o-azidobenzoyl chloride 
• 147-85-3 L-proline 

Downstream Products

• 923973-16-4 (11aS)-10-n-butyl-2,3-dihydro-1H-pyrrolo[2,1-c][1,4]benzodiazepine-5,11-(10H,11aH)-dione 
• 1318978-86-7 (S)-methyl 1-(2-(butylamino)benzoyl)pyrrolidine-2-carboxylate 
• 72435-89-3 (11aS)-1,2,3,11a-tetrahydro-5H-pyrrolo[2,1-c][1,4]benzodiazepin-5-one 
• 166451-13-4 1-(2'-azidobenzoyl)pyrrolidine-2-carbaldehyde 
• 24919-40-2 (S)-1,2,3,11a-tetrahydro-5H-pyrrolo[2,1-c][1,4]benzodiazepine-5,11(10H)-dione 
• 166451-15-6 methyl N-<2-(triphenylfosforanylidene)aminobenzoyl>pyrrolidine-2-carboxylate 

Relevant articles and documents

Catalytic Staudinger/aza-Wittig sequence by in situ phosphane oxide reduction

A Staudinger/aza-Wittig reaction sequence is described that is catalytic in phosphorus. Towards this end, the phosphane oxide is reduced in situ by diphenylsilane, which allows for substoichiometric amounts of the catalyst 5-phenyldibenzophosphole to be used. The substrate scope is investigated and benzoxazoles, benzodiazepine imidates and a 2-methoxypyrrole were successfully synthesized. These investigations show that a fast aza-Wittig reaction is required to obtain high yields. A catalytic Staudinger/aza-Wittig reaction sequence, involving in situ phosphane oxide reduction, was successfully developed. Benzoxazoles, benzodiazepine imidates and 2-methoxypyrrole were synthesized without phosphane oxide waste products. Copyright

One pot conversion of azido arenes to N-arylacetamides and N-arylformamides: Synthesis of 1,4-benzodiazepine-2,5-diones and fused [2,1-b]quinazolinones

Sodium iodide in acidic media has been employed for the synthesis of N-arylformamides and N-arylacetamides. The NaI/acetic acid reagent system has also been extended for the synthesis of 1,4-benzodiazepine-2,5-diones, pyrrolo[2,1-c][1,4]benzodiazepine-5,11-diones, and fused [2,1-b]quinazolinones.

Synthesis of pyrrolo[2,1-c][1,4]benzodiazepine antibiotics via azido reductive cyclization with HMDST

A new facile synthesis of pyrrolo[2,1-c][1,4]benzodiazepine (PBD) ring system has been achieved by reductive cyclization of the azide employing hexamethyldisilathiane (HMDST). The parent unsubstituted PBD and the natural product DC-81 have also been prepared in good overall yields.