36060-84-1

Basic information

• Product Name: AC-PHG-OME
• Synonyms: AC-PHENYLGLYCINE-OME;AC-PHG-OME;ACETYL-L-PHENYLGLYCINE METHYL ESTER;N-ALPHA-ACETYL-L-PHENYLGLYCINE-OME
• CAS NO: 36060-84-1
• Molecular Formula: C₁₁H₁₃NO₃
• Molecular Weight: 207.23
• Mol File: 36060-84-1.mol

Chemical Properties

• Appearance: /
• Storage Temp.: 2-8°C
• CAS DataBase Reference: AC-PHG-OME(CAS DataBase Reference)
• NIST Chemistry Reference: AC-PHG-OME(36060-84-1)
• EPA Substance Registry System: AC-PHG-OME(36060-84-1)

Safety Data

• Hazardous Substances Data: 36060-84-1(Hazardous Substances Data)

Upstream product

• 67-56-1 methanol 
• 1426822-96-9 C₁₂H₁₂F₃NO₃ 
• 1176466-67-3 (1S,1'S)-1,1'-(1-acetyl-1H-1,2,4-triazole-3,5-diyl)-bis(ethane-1,1-diyl) diacetate 
• 15028-40-7 DL-2-phenylglycine methyl ester hydrochloride 
• 15028-39-4 L-2-phenylglycine methyl ester hydrochloride 
• 108-24-7 acetic anhydride 
• 60676-51-9 methyl (Z)-2-(acetylamino)-3-phenylpropenoate 
• 100508-77-8 2-(Acetylimino)-2-phenylessigsaeure-methylester 

Downstream Products

• 1126635-25-3 L-(+)-N-Ac-phenylglycine hydrazide 

Relevant articles and documents

Carica papaya lipase catalysed resolution of β-amino esters for the highly enantioselective synthesis of (S)-dapoxetine

An efficient synthesis of the (S)-3-amino-3-phenylpropanoic acid enantiomer has been achieved by Carica papaya lipase (CPL) catalysed enantioselective alcoholysis of the corresponding racemic N-protected 2,2,2-trifluoroethyl esters in an organic solvent. A high enantioselectivity (E > 200) was achieved by two strategies that involved engineering of the substrates and optimization of the reaction conditions. Based on the resolution of a series of amino acids, it was found that the structure of the substrate has a profound effect on the CPL-catalysed resolution. The enantioselectivity and reaction rate were significantly enhanced by switching the conventional methyl ester to an activated trifluoroethyl ester. When considering steric effects, the substituted phenyl and amino groups should not both be large for the CPL-catalysed resolution. The mechanism of the CPL-catalysed enantioselective alcoholoysis of the amino acids is discussed to delineate the substrate requirements for CPL-catalysed resolution. Finally, the reaction was scaled up, and the products were separated and obtained in good yields (≥ 80 %). The (S)-3-amino-3- phenylpropanoic acid obtained was used as a key chiral intermediate in the synthesis of (S)-dapoxetine with very high enantiomeric excess (> 99 %). A carica papaya lipase catalysed resolution of N-protected β-phenylalanine esters has been developed. High enantioselectivity was achieved by two strategies that involved engineering of the substrates and optimization of the reaction conditions. After 50 % conversion, the products were separated and used as key chiral intermediates for the synthesis of (S)-dapoxetine with > 99 % ee. Copyright

Chiral 1,2,4-triazoles: stereoselective acylation and chlorination

Acyl groups are transferred from diverse N- and O-acyl derivatives of chiral 3,5-bis-(1-hydroxyethyl)-[1,2,4]-triazole to amino acid esters enantioselectively, with 7% to 68% ee, depending on the temperature conditions and nature of the reagents. Thionyl

An efficient synthesis of new 2-aminomethyl-1,3,4-oxadiazoles from enantiomeric phenylglycine hydrazides

New derivatives of 2-aminomethyl-1,3,4-oxadiazole were synthesized in the reactions of N-protected phenylglycine hydrazides and triethyl orthoesters (orthoformate, orthoacetate, orthopropionate, orthobenzoate) in the presence of glacial acetic acid. Studies on the cleavage reactions of the acid-sensitive N-BOC and N-Ac 1,3,4-oxadiazoles are presented. Spectral characteristics of the compounds and attempts to elucidate the racemization phenomenon observed in products are also discussed.

On the economic application of DuPHOS rhodium(I) catalysts: A comparison of COD versus NBD precatalysts

The effectiveness of cyclooctadiene and norbornadiene precatalysts of the type [Rh(DuPHOS)(diolefin)]BF4 in catalytic asymmetric hydrogenation of various prochiral olefins has been examined. In some of the systems studied, the NBD complex gave

Rational de novo design of NADH mimic for stereoselective reduction based on molecular orbital calculation

The methodology of rational design of NADH mimics in stereoselective reduction of carbonyl and imino groups based on molecular orbital calculation was described. The designed NADH mimics 1a and 1b were subjected to the reduction of benzoylformate and acetyliminophenylacetate. As expected from the calculations of the transition-states, the reduction with 1a proceeded with high stereoselectivity in both substrates, while 1b showed much lower chirality transfer.