111492-26-3

Basic information

• Product Name: Alanine, N-(hydroxyphenylacetyl)-2-methyl- (9CI)
• Synonyms: Alanine, N-(hydroxyphenylacetyl)-2-methyl- (9CI)
• CAS NO: 111492-26-3
• Molecular Formula: C₁₂H₁₅NO₄
• Molecular Weight: 237.25
• Mol File: 111492-26-3.mol
• Article Data: 3

Chemical Properties

• Appearance: /
• CAS DataBase Reference: Alanine, N-(hydroxyphenylacetyl)-2-methyl- (9CI)(CAS DataBase Reference)
• NIST Chemistry Reference: Alanine, N-(hydroxyphenylacetyl)-2-methyl- (9CI)(111492-26-3)
• EPA Substance Registry System: Alanine, N-(hydroxyphenylacetyl)-2-methyl- (9CI)(111492-26-3)

Safety Data

• Hazardous Substances Data: 111492-26-3(Hazardous Substances Data)

Upstream product

• 111492-13-8 (+/-)-2-(2-hydroxy-2-phenylacetamido)-N,N,2-trimethylpropionamid 

Downstream Products

• 87866-94-2 (+/-)-2-<2-<2-<2-(2-hydroxy-2-phenylacetamido)-2-methylpropionamido>-2-methylpropionamido>-2-methylpropionamido>-N,N,2-trimethylpropionamid 
• 87866-97-5 3,3,6,6,9,9,12,12-octamethyl-15-phenyl-1-oxa-4,7,10,13-tetraazacyclopentadecan-2,5,8,11,14-penton 
• 87872-95-5 (+/-)-2-<2-<2-(2-hydroxy-2-phenylacetamido)-2-methylpropionamido>-2-methylpropionamido>-N,N,2-trimethylpropionamid 
• 112142-64-0 (+/-)-2-<2-<2-(2-hydroxy-2-phenylacetamido)-2-methylpropionamido>-2-methylpropionamido>-2-methylpropionsaeure 
• 87866-96-4 (+/-)-3,3,6,6,9,9-hexamethyl-12-phenyl-1-oxa-4,7,10-triazacyclododecan-2,5,8,11-tetron 
• 112142-59-3 (+/-)-2-<2-(2-hydroxy-2-phenylacetamido)-2-methylpropionamido>-2-methylpropionsaeure 
• 87872-96-6 (+/-)-3,3,6,6-tetramethyl-9-phenyl-1-oxa-4,7-diazacyclononan-2,5,8-trion 

Relevant articles and documents

3-(Dimethylamino)-2,2-dimethyl-2H-azirine as an α-Aminoisobutyric-Acid (Aib) Equivalent: Cyclic Depsipeptides via Direct Amide Cyclization

In MeCN at room temperature, 3-(dimethylamino)-2,2-dimethyl-2H-azirine (1) and α-hydroxycarboxylic acids react to give diamides of type 8.Selective cleavage of the terminal N,N-dimethylcarboxamide group in MeCN/H2O leads to the corresponding carboxylic acids 13.In toluene/PhSH, phenyl thioesters of type 11 are formed.Starting with diamides 8, the formation of morpholin-2,5-diones 10 has been achieved either by direct amide cyclization via intermediate 1,3-oxazol-5(4H)-ones 9 or via base-catalyzed cyclization of the phenyl thioesters 11.Reaction of carboxylic acids with 1, followed by selective amide hydrolysis, has been used for the construction of peptides from α-hydroxy carboxylic acids and repetitive α-aminoisobutyric-acid (Aib) units.Cyclization of 14a, 17a, and 20a with HCl in toluene at 100 deg C gave the 9-, 12-, and 15-membered cyclic depsipeptides 15, 18, and 21, respectively.

3-DIMETHYLAMINO-2,2-DIMETHYL-2H-AZIRIN ALS Aib-AEQUIVALENT BEI HETEROCYCLENSYNTHESEN; SYNTHESE VON 6-, 9-, 12- UND 15-GLIEDRIGEN RINGEN

The cyclization reaction of the dimethylamides 2b, 5, 6 and 7, resulting from the reaction of mandelic acid with the aminoazirine 1, yields the 6-, 9-, 12- and 15-membered cyclic depsipeptides 10 - 13, respectively.