Benzoyl amide

In 1909, Claisen described the first such reaction. Treating 2,5-di-methylisoxazolium methosulfate (140) with potassium benzoate in aqueous media he obtained the iV-methyl-iV-benzoyl amide (141) of acetoacetic acid. ... 

The first-generation synthesis of levetiracetam (3), as shown in Scheme 14.9 [29], starts with benzoyl protection and oxidation of (S)-aminobutanol (32), which gives rise to the corresponding N-benzoyl protected (S)-aminobutyric acid (33). After N-benzoyl amidation and deprotection, (S)-aminobutyramide (34) is obtained. Chemoselective butyrolactam ring formation using the intermediate 34 and 4-chlorobutyryl chloride finally affords levetiracetam (3). 

Benzamide Benzoyl amide Benzene Carbon Amide or Benzoic Acid Amidefcailed Benzamid or Benzol-saure-amid in Ger), CgH6.CO.NH2 mw 121.13,... 

Examples Toluidines, nitroanilines, amino benzoyl amides, and the sulfonic acids thereof. 

For subsequent transformations, it was necessary to protect the amino and C-2 carboxyl groups of fra/w-4-hydroxy-L-proline 34. Throughout all of the synthetic work to be described, A-benzoyl amide protection was chosen as it was felt likely that such a functional group would be resistant to most reaction conditions. Initially, a C-2 terf-butyl ester was chosen in an attempt to maximize the stereoselectivity in the planned enamine alkylation reaction however, later experiments revealed that the more straightforward to introduce C-2 methyl ester was equally effective. The preparations for all of the derivatives used are described here. 

The phosphazene bases BTPP and Bu-P2 mediate the rearrangement of unactivated A -alkyl-(9-benzoyl hydroxamic acid derivatives to give 2-benzoyl amides. The rate of reaction was found to be dependent upon the steric nature of the A -alkyl substituent [39a]. Treatment of malonyl derived (9-acyUiydroxamic acid derivatives with the phosphazene superbase Bu-P2 gives 2,3-dihydro-4-isoxazole carboxylic ester derivatives. The rate and yield of the reaction depend upon the (9-acyl substituent [36b] (Scheme 5.21). 

Oil of bitter almonds Crystalline benzoic acid Anhydrous benzoic acid Benzoyl chloride Benzamide ( or more correctly benzoyl amide )... 

In the majority of cases, hydroxylation by Beauveria bassiana occurs in a regioselective manner, but high enantioselectivity is not always observed. As shown in Scheme 2.152, both enantiomers of the A -benzyl-protected bicyclic lactam are hydroxylated with high regioselectivity in position 11, but the reaction showed very low enantioselectivity. On the other hand, when the lactam moiety was replaced by a more polar benzoyl-amide, which functions as polar anchor group, high enantiodifferentiation occurred. The (l/ )-enantiomer was hydroxylated at carbon 12 and the (IS)-counterpart gave the 11-hydroxylated product [1116]. A minor amount of 6-exo-alcohol was formed with low enantiomeric excess. 

The reaction of 1 equiv of racemic amines was carried out with 0.5 equiv of (S)-51 to furnish the corresponding chiral N-benzoylated amines with good conversion (48-50%) and selectivity factor (25-60). The (S)-isomer of 51 produced the (S) isomer of the benzoylated amines. The unreacted amines were further converted to N-benzoyl amides and found to possess (J )-configuration. 

Metho -4-methyl-benzoe8iuTe-benzoyl< amid 10 II140. 

Removal of C-terminal peptide amides from a 3-nitro-4-aminomethyl-benzoyl amide resin by photolysis."... 

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