76311-95-0

Basic information

• Product Name: methyl 3-(methylamino)-3-oxopropanoate
• Synonyms: methyl 3-(methylamino)-3-oxopropanoate
• CAS NO: 76311-95-0
• Molecular Formula: C₅H₉NO₃
• Molecular Weight: 131.12986
• Mol File: 76311-95-0.mol
• Article Data: 6

Chemical Properties

• Appearance: /
• CAS DataBase Reference: methyl 3-(methylamino)-3-oxopropanoate(CAS DataBase Reference)
• NIST Chemistry Reference: methyl 3-(methylamino)-3-oxopropanoate(76311-95-0)
• EPA Substance Registry System: methyl 3-(methylamino)-3-oxopropanoate(76311-95-0)

Safety Data

• Hazardous Substances Data: 76311-95-0(Hazardous Substances Data)

Usage

General Description

Methyl 3-(methylamino)-3-oxopropanoate, also known as Methyl N-methylglycinate, is a chemical compound with the molecular formula C5H9NO3. It is a white crystalline solid that is commonly used as an intermediate in the synthesis of pharmaceuticals, organic compounds, and agrochemicals. methyl 3-(methylamino)-3-oxopropanoate is also used as a reagent in organic synthesis and as a building block in the production of active pharmaceutical ingredients. Methyl 3-(methylamino)-3-oxopropanoate is considered to be moderately hazardous to human health and the environment, and proper safety precautions should be taken when handling and using this chemical.

Upstream product

• 6186-89-6 ethyl methyl malonate 
• 593-51-1 methylamine hydrochloride 
• 16695-14-0 Malonic acid monomethyl ester 
• 74-89-5 methylamine 
• 67-56-1 methanol 
• 42105-98-6 3-(methylamino)-3-oxopropanoic acid 
• 37517-81-0 3-chloro-3-oxopropanoic acid methyl ester 

Downstream Products

• 511284-18-7 dimethyl-4-(4-fluorophenyl)-1-methyl-2,6-dioxo-3,5-piperidinedicarboxylate 
• 188302-27-4 (3S,4R)-4-(4-fluorophenyl)-1-methyl-2,6-dioxopiperidine-3-carboxylic acid methyl ester 
• 1099628-85-9 meso-(3R,4s,5S)-bis(3-hydroxypropyl) 4-(4-fluorophenyl)-1-methyl-2,6-dioxopiperidine-3,5-dicarboxylate 
• 1099628-83-7 meso-(3R,4s,5S)-bis(2-hydroxyethyl) 4-(4-fluorophenyl)-1-methyl-2,6-dioxopiperidine-3,5-dicarboxylate 
• 1099628-81-5 meso-(3R,4s,5S)-bis(2-methoxyethyl) 4-(4-fluorophenyl)-1-methyl-2,6-dioxopiperidine-3,5-dicarboxylate 
• 1099629-11-4 C₁₆H₁₈FNO₅ 
• 1099629-09-0 C₁₅H₁₆FNO₅ 
• 188302-25-2 (3S,4R)-3-ethoxycarbonyl-4-(4-fluorophenyl)-N-methylpiperidine-2,6-dione 

Relevant articles and documents

Asymmetric Synthesis of α,β-Epoxy-?-lactams through Tandem Darzens/Hemiaminalization Reaction

A catalytic asymmetric tandem Darzens/hemiaminalization reaction of glyoxals with α-bromo-β-esteramides or α-bromo-β-ketoamide was accomplished in the presence of a chiral N,N′-dioxide/Yb(III) complex. Various chiral α,β-epoxy-?-lactams were obtained in moderate to good yields with excellent diastereo- and enantioselectivities. The versatility of the transformation is illustrated in the formal synthesis of berkeleyamide D.

Unsymmetrical vic-tricarbonyl compounds for the total syntheses of cladoniamide G and cladoniamide F

A 2-unsubstituted indole adds under Cu-box-catalysis to mesoxalic ester amides with high enantioselectivity, whereas low enantiomeric excess is obtained for 2-substituted indoles. A mesoxalic ester amide is used as key component in the total syntheses of alkaloids cladoniamide G and cladoniamide F. The natural product syntheses involve Suzuki cross-coupling to a 2,2′-biindole, arylation of the vic-tricarbonyl compound, and intramolecular lactam formation. Copyright

Conformation-directing effects of a single intramolecular amide-amide hydrogen bond: Variable-temperature NMR and IR studies on a homologous diamide series

We have studied intramolecular hydrogen bonding in a homologous series of diamides (compounds 1-6) in methylene chloride, 9:1 carbon tetrachloride/benzene, and acetonitrile. By correlating variable-temperature 1H NMR and IR measurements, we have shown that the temperature dependence of the amide proton NMR chemical shift (Δδ/ΔT) can provide qualitative (and in some cases quantitative) information on the thermodynamic relationship between the intramolecularly hydrogen bonded and non-hydrogen-bonded states of flexible molecules. Among the hydrogen-bonded ring sizes represented in the diamide series, the intramolecular interaction is particularly enthalpically favorable in the nine-membered hydrogen-bonded ring (compound 4). Variable-temperature IR and NMR data indicate that the internally hydrogen bonded state of diamide 4 is 1.4-1.6 kcal/mol more favorable enthalpically than the non-hydrogen-bonded state, in methylene chloride solution; the non-hydrogen-bonded state is 6.8-8.3 eu more favorable entropically in this solvent. In contrast, there appear to be much smaller enthalpy differences between the internally hydrogen bonded and non-hydrogen-bonded states of diamides 2 and 3. Our findings are important methodologically because the temperature dependences of amide proton chemical shifts are commonly used to elucidate peptide conformation in solution. Our results show that previous "rules" for the interpretation of such data are incomplete. In non-hydrogen-bonding solvents, small amide proton Δδ/ΔT values have been taken to mean that the proton is either entirely free of hydrogen bonding or completely locked in an intramolecular hydrogen bond over the temperature range studied. We demonstrate that an amide proton can be equilibrating between intramolecularly hydrogen bonded and non-hydrogen-bonded states and still manifest a small chemical shift temperature dependence (implying that the hydrogen-bonded and non-hydrogen-bonded states are of similar enthalpy).