199928-80-8

Basic information

• Product Name: 2-Azido-N,N-dimethyl-2-phenyl-acetamide
• CAS NO: 199928-80-8
• Molecular Weight: 204.231
• Mol File: 199928-80-8.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: 2-Azido-N,N-dimethyl-2-phenyl-acetamide(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Azido-N,N-dimethyl-2-phenyl-acetamide(199928-80-8)
• EPA Substance Registry System: 2-Azido-N,N-dimethyl-2-phenyl-acetamide(199928-80-8)

Safety Data

• Hazardous Substances Data: 199928-80-8(Hazardous Substances Data)

Upstream product

• 10507-52-5 benzyl N,N-dimethylcarbamate 

Downstream Products

• 1161012-23-2 2-Amino-N,N-dimethyl-2-phenyl-acetamide 

Relevant articles and documents

An Unexpected Transformation of Benzyl Carbamates into α-Azidobenzeneacetamides

Successive treatment of benzyl carbamates 5 (Z-protected secondary amines) with lithium diisopropylamide (LDA), diphenyl phosphorochloridate (DPPCl), and NaN3 yielded the corresponding α-azidobenzeneacetamides 6 in 45-50% yield (Schemes 2 and 3). In the case of Z-protected diisopropylamine 5b, the phosphate 7 was isolated as a minor product. A reaction mechanism for this unexpected transformation is proposed in Scheme 4, the key step being the ring closure of a benzylic anion to give an oxirane intermediate B. In cursory experiments, it was demonstrated that α-azidobenzeneacetamides 6 can be used as 2-phenylglycine synthons in the formation of dipeptides by using a phosphine-mediated coupling (Scheme 5).