188777-45-9

Basic information

• Product Name: Hydrazinecarboxylic acid, 2-[(1S)-1-carboxyethyl]-2-(phenylmethyl)-, 1-(1,1-dimethylethyl) ester
• CAS NO: 188777-45-9
• Molecular Formula: C15H22N2O4
• Molecular Weight: 294.351
• Mol File: 188777-45-9.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: Hydrazinecarboxylic acid, 2-[(1S)-1-carboxyethyl]-2-(phenylmethyl)-, 1-(1,1-dimethylethyl) ester(CAS DataBase Reference)
• NIST Chemistry Reference: Hydrazinecarboxylic acid, 2-[(1S)-1-carboxyethyl]-2-(phenylmethyl)-, 1-(1,1-dimethylethyl) ester(188777-45-9)
• EPA Substance Registry System: Hydrazinecarboxylic acid, 2-[(1S)-1-carboxyethyl]-2-(phenylmethyl)-, 1-(1,1-dimethylethyl) ester(188777-45-9)

Safety Data

• Hazardous Substances Data: 188777-45-9(Hazardous Substances Data)

Upstream product

• 150884-51-8 1,1-dimethylethyl N-[(4-cyanophenyl)methylen]carbamate 
• 68014-21-1 triphenyl(t-butoxycarbonylimino)phosphorane 
• 1070-19-5 N-(tert-butyloxycarbonyl) azide 
• 100-52-7 benzaldehyde 
• 219547-77-0 t-butyl 3-(trichloromethyl)-1,2-oxaziridine-2-carboxylate 
• 7585-47-9 N-benzyl-(S)-alanine 
• 150884-56-3 N-tert-butyloxycarbonyl-3-(4-cyanophenyl)oxaziridine 

Downstream Products

• 188777-60-8 Boc-NH(Bzl)Ala-Ala-NHⁱPr 
• 672306-73-9 methyl (S)-2-[1-benzyl-2-((S)-2-{1-benzyl-2-[(tert-butoxy)carbonyl]hydrazino}propionyl)hydrazino]-4-methylpentanoate 

Relevant articles and documents

Electrophilic Amination of Amino Acids with N-Boc-oxaziridines: Efficient Preparation of N-Orthogonally Diprotected Hydrazino Acids and Piperazic Acid Derivatives

A general two-step preparation of enantiopure Nα,N β-orthogonally diprotected α-hydrazino acids 1 is developed on a multigram scale. The key reaction is the efficient electrophilic amination of N-benzyl amino acids 6 with N-Boc-oxaziridine 7 and accommodates various functional groups encountered in side chains of amino acids. The cyclic 2,3,4,5-tetrahydro-3-pyridazine carboxylic acid (piperazic acid) derivatives 2 and 3 or the cyclic 3,4-dihydro-3-pyrazolecarboxylate 4 are conveniently prepared from glutamic acid or aspartic acid via orthogonally diprotected α-hydrazino acids 1m and 1n.

N-alkyloxycarbonyl-3-aryloxaziridines: Their preparation, structure, and utilization as electrophilic amination reagents

This paper reports the synthesis of a series of N-protected oxaziridines (N-Moc, Boc, Z or Fmoc) and discusses their ability to deliver their N-alkoxycarbonyl fragment to amines, enolates, sulfur, and phosphorus nucleophiles (electrophilic amination). These oxaziridines are prepared by oxidation of the corresponding imines with oxone or anhydrous MCPBA lithium salt as the source of oxygen. They transfer their N-protected fragment to primary and secondary amines to give protected hydrazines in fair to excelent yield. The nitrogen transfer to free amino acids (in form of their R4N+ salts) is particularly fast, even at low temperature, providing L (or D) N-protected α-hydrazino acids. Enolates are C-aminated to give N-protected α-amino ketones, esters, or amides in modest yield, due to a side aldol reaction of the unreacted enolate with the released benzaldehyde. With tertiary amines (Et3N), sulfides (PhSMe), and phosphines (Ph3P), amination and oxidation proceed in a parallel way; the amount of amination product increases when the temperature is lowered (kinetic control). Some of the factors that can orient the oxaziridine reactivity towards amination or oxidation of nucleophiles are considered.