103808-45-3

Basic information

• Product Name: (S)-N-benzyl-2-hydroxypropionamide
• Synonyms: (S)-N-benzyl-2-hydroxypropionamide
• CAS NO: 103808-45-3
• Molecular Weight: 179.219
• Mol File: 103808-45-3.mol
• Article Data: 19

Chemical Properties

• CAS DataBase Reference: (S)-N-benzyl-2-hydroxypropionamide(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-N-benzyl-2-hydroxypropionamide(103808-45-3)
• EPA Substance Registry System: (S)-N-benzyl-2-hydroxypropionamide(103808-45-3)

Safety Data

• Hazardous Substances Data: 103808-45-3(Hazardous Substances Data)

Upstream product

• 79-33-4 L-Lactic acid 
• 100-46-9 benzylamine 
• 687-47-8 (S)-Ethyl lactate 
• 56777-24-3 benzyl (S)-Lactate 
• 27871-49-4 (S)-Methyl lactate 
• 105-38-4 vinyl propionate 
• 88333-03-3 Benzyl isocyanide 
• 6653-71-0 N-benzyl-2-bromopropanamide 

Downstream Products

• 503185-02-2 (S)-O-acryloyl-N-benzyllactamide 
• 1360567-29-8 1-(benzylamino)-1-oxopropan-2-yl methanesulfonate 
• 1413930-76-3 (S)-ethyl 5-(benzylamino)-4-methylpent-2-ynoate 
• 1349191-61-2 (S)-3-benzyl-5-methyl-1,2,3-oxathiazolidine 2,2-dioxide 
• 68259-66-5 N-benzyl-2-oxopropanamide 
• 130627-47-3 (2S)-4-(2,5-Dimethoxy-3,4,6-trimethylphenyl)-2-hydroxy-2-methylbutansaeure-<(1S)-1-(benzylcarbamoyl)-ethyl>ester 
• 120800-87-5 (S)-4-benzyl-6-methylmorpholin-3-one 
• 120800-89-7 (S)-4-benzyl-2-methylmorpholine 
• 118460-12-1 (S)-4-benzyl-6-methylmorpholin-2-one 

Relevant articles and documents

DOTMA-based amides (DOTMAMs) as a platform for the development of PARACEST MRI contrast agents

A synthetic methodology leading to previously unknown DOTMA-based secondary amides (DOTMAMs) has been developed. Alkylation of cyclen with l-lactic acid-derived pseudohalides was used as a key step affording the alkyl- and aryl-decorated DOTMAMs. Amino acid-decorated DOTMAMs were obtained via peptide coupling between DOTMA and protected amino acids. Metallation of the DOTMAMs ligand with Tm3+ gave complexes exhibiting proximal amide proton based paramagnetic CEST effects at -50 ppm relative to water.

Stereoselective Pseudomonas cepacia lipase mediated synthesis of α-hydroxyamides

A new method for the synthesis of α-hydroxyamides via the Pseudomonas cepacia lipase catalyzed amidation of α-hydroxyesters in non-aqueous media is described. Reactivities of α-hydroxy benzyl esters are excellent, resulting in rapid conversions to good yields of α-hydroxyamides, while ethyl and methyl esters react more slowly, and some hindered esters show no reactivity under the conditions studied. Some benzyl esters react stereoselectively, producing excellent yields of asymmetric α-hydroxyamides.

Amidation of unactivated ester derivatives mediated by trifluoroethanol

A catalytic amidation protocol mediated by 2,2,2-trifluoroethanol has been developed, facilitating the condensation of unactivated esters and amines, furnishing both secondary and tertiary amides. The complete scope and limitations of the method are described, along with modified conditions for challenging substrates such as acyclic secondary amines and chiral esters with retention of chiral integrity.

A [3+3] cyclization strategy for asymmetric synthesis of alkyl substituted piperidine-2-ones using 1,2-cyclic sulfamidates: A formal synthesis of (S)-coniine from l-norvaline

Regioselective ring-opening reactions of a set of representative 1,2-cyclic sulfamidates with lithium triethylorthopropiolate proceeded efficiently to deliver the corresponding δ-amino-α,β-unsaturated esters after acidic hydrolysis. Hydrogenation of the unsaturated esters and subsequent thermal cyclization afforded the related alkyl substituted piperidine-2-ones. This approach represents a novel [3+3] cyclization strategy for the asymmetric synthesis of alkyl substituted piperidin-2-ones. Efficiency of the cyclization process is illustrated by a formal asymmetric synthesis of (S)-coniine from l-norvaline.