171775-72-7

Upstream product

• 14028-61-6 potassium (R)-2,2-dimethyl-1,3-dioxolane-4-carboxylate 
• 530-62-1 1,1'-carbonyldiimidazole 
• 100-46-9 benzylamine 
• 52373-72-5 methyl (R)-2,2-dimethyl-1,3-dioxolane-4-carboxylate 
• 114746-70-2 (R)-2,2-dimethyl-[1,3]dioxolane-4-carboxylic acid 
• 22323-82-6 (S)-(+)-(2,2-dimethyl-[1,3]dioxolan-4-yl)methanol 
• 183967-78-4 N-benzyl-1-cyano-1-deoxy-1-((trimethylsiloxy)amino)-2,3-O-isopropylidene-D-threo-triitol 

Downstream Products

• 205122-65-2 (R)-N-benzyl 2,3-dihydroxypropionamide 

Relevant academic research and scientific papers

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.

Accessing N-Acyl Azoles via Oxoammonium Salt-Mediated Oxidative Amidation

An operationally simple, robust, metal-free approach to the synthesis of N-acyl azoles from both alcohols and aldehydes is described. Oxidative amidation is facilitated by a commercially available organic oxidant (4-acetamido-2,2,6,6-tetramethylpiperidine-1-oxoammonium tetrafluoroborate) and proceeds under very mild conditions for an array of structurally diverse substrates. Tandem reactions of these activated amides, such as transamidation and esterification, enable further elaboration. Also, the spent oxidant can be recovered and used to regenerate the oxoammonium salt.

Propionamide anticonvulsants

The present invention is directed to a compound of the following formula: STR1 pharmaceutical compositions containing the same and the use thereof as an anticonvulsant.

The anticonvulsant activities of N-benzyl 3-methoxypropionamides

We recently reported that the ED50 value for (R,S)-2,3- dimethoxypropionamide (1) in the maximal electroshock (MES)-induced seizure test in mice was 30 mg/kg (Choi, D.; Stables, J.P., Kohn, H. Bioorg. Med. Chem. 1996, 4, 2105). This value is comparable to that observed for phenobarbital (ED50 = 22 mg/kg). Compound 1 is structurally similar to a class of MES-selective anticonvulsant agents, termed functionalized amino acids (2), that were developed in our laboratory. The distinguishing feature of 2 is the differential activities observed for enantiomers. In this study, we asked whether comparable differences in activities were observed in the MES-induced seizure test for (R)- and (S)-1. We developed stereospecific syntheses for these enantiomers and showed that both compounds exhibit nearly equal anticonvulsant activity in mice (ip) (MES ED50 = 79-111 mg/kg). The surprisingly high ED50 values for (R)- and (S)-1 required our redetermining the ED50 value for (R,S)-1. We revised this value to 79 mg/kg. A limited structure-activity relationship study for 1 was conducted. Special attention was given to the C(2) methoxy unit in 1. We found that replacement of this moiety led to only modest differences in the MES activities upon ip administration to mice. Significantly, we observed an enhancement in the anticonvulsant activity for (R,S)-N-benzyl 2-hydroxy-3-methoxypropionamide ((R,S)-6) upon oral administration to rats ((R,S)-6: mice (ip) ED50 > 100, 50 = 62 mg/kg). The activities of 3- methoxypropionamides, functionalized amino acids, and related compounds are discussed. (C) 1999 Elsevier Science Ltd.

Stereoselective addition of cyanide reagents to nitrones

An exploration of the diastereoselective addition of cyanide reagents to the nitrone 1 derived from D-glyceraldehyde acetonide to afford mixtures of syn-2 and anti-2 is presented. Trimethylsilyl cyanide was found to add to the nitrone 1 with essentially complete syn-stereoselectivity in excellent yields.