39057-61-9

Upstream product

• 67-56-1 methanol 
• 23624-82-0 N-chloro-N-benzylacetamide 
• 73289-49-3 methyl N-acetylbenzoimidate 
• 64-19-7 acetic acid 
• 7471-86-5 methyl benzimidate 
• 85199-41-3 dimethyl-N,N'-sulfinyl-dibenzoimidate 
• 14257-84-2 N-acetyl-α-phenylglycine 
• 100-52-7 benzaldehyde 

Downstream Products

• 1033076-09-3 C₁₄H₁₇NO₂ 

Relevant academic research and scientific papers

Synthesis of N-Acyl-N,O-acetals from Aldehydes, Amides and Alcohols

A general synthesis of N-acyl-N,O-acetals from aldehydes, amides and alcohols is reported. This new method consists of two single steps: (a) magnesium-mediated addition of an amide or carbamate to an aldehyde and (b) acid-catalyzed conversion of the N-acylhemiaminal to the N-acyl-N,O-acetal. This two-step protocol allows the multigram synthesis of various N-acyl-O-alkyl-N,O-acetals.

α-amidoalkylating agents from N-acyl-α-amino acids: 1-(N-acylamino)alkyltriphenylphosphonium salts

N-Acyl-α-amino acids were efficiently transformed in a two-step procedure into 1-N-(acylamino)alkyltriphenylphosphonium salts, new powerful α-amidoalkylating agents. The effect of the α-amino acid structure, the base used [MeONa or a silica gel-supported piperidine (SiO 2-Pip)], and the main electrolysis parameters (current density, charge consumption) on the yield and selectivity of the electrochemical decarboxylative α-methoxylation of N-acyl-α-amino acids (Hofer-Moest reaction) was investigated. For most proteinogenic and all studied unproteinogenic α-amino acids, very good results were obtained using a substoichiometric amount of SiO2-Pip as the base. Only in the cases of N-acylated cysteine, methionine, and tryptophan, attempts to carry out the Hofer-Moest reaction in the applied conditions failed, probably because of the susceptibility of these α-amino acids to an electrochemical oxidation on the side chain. The methoxy group of N-(1-methoxyalkyl)amides was effectively displaced with the triphenylphosphonium group by dissolving an equimolar amount of N-(1-methoxyalkyl)amide and triphenylphosphonium tetrafluoroborate in CH 2Cl2 at room temperature for 30 min, followed by the precipitation of 1-N-(acylamino)alkyltriphenylphosphonium salt with Et 2O.

STEREOCONTROLLED TOTAL SYNTHESIS OF (+)-PEDERINE

A mild one-pot method for the synthesis of acyclic N-(1-methoxyalkyl)amides starting from carboxylic acid and methyl imidates has been developed and applied to the first total synthesis of (+)-pederine (1), a potent insect poison.Furthermore, the stereocontrolled total synthesis of 1 was also achieved by employing acid catalyzed double alkoxy-exchange reaction of N-(1-methoxyalkyl)amide group as key step.

Photolytic Dehydrochlorination of N-Chloro-N-alkyl Amides: Formaton of N-(α-Methoxyalkyl) Amides

The photoinduced dehydrochlorination, in methanol, of N-chloro-N-alkyl amides with one substitient at the α position to nitrogen gave good yields of N-(α-methoxyalkyl) amides and the parent amides as secondary products.N-Chloro amides disubstituted at the α position gave mostly parent amides.In most cases no products resulting from 1,5 hydrogen transfer of amidyl radicals were observed.The quantum yields of decomposition of N-chloro-N-methylpentanamide (1a) were significantly greater than unity, indicative of a chain process for dehydrochlorination.The reaction was affected by the solvent, addition of base or radical inhibitors, concentration of N-chloro amide, light intensity, and irradiation wavelenght.

TOTAL SYNTHESIS OF (+)-PEDERINE. A SIMPLE SYNTHETIC METHOD FOR N-(1-METHOXYALKYL)AMIDES

A mild one-pot method for the synthesis of acyclic N-(1-methoxyalkyl)amides starting from carboxylic acids and methyl imidates had been developed and applied to the total synthesis of the insect poison pederine 1.