141694-25-9Relevant articles and documents
Synthesis of various acylating agents directly from carboxylic acids
Pilathottathil, Fathima,Vineet Kumar, Doppalapudi,Kaliyamoorthy, Alagiri
supporting information, p. 1622 - 1632 (2020/04/27)
A straightforward synthesis of acylating reagents such as Weinreb and MAP amides from aromatic, aliphatic carboxylic acids, and amino acids using PPh3/NBS combination is described. A chemo-selective modification of the carboxylic acid group into Weinreb amide in the presence of more reactive aldehydes and ketones is presented. All reactions were performed at ambient temperature under air using undried commercial grade solvent. Furthermore, the present methodology could be performed at a gram scale under inert-free reaction conditions. In addition, 7-azaindoline amide auxiliary (used for catalytic asymmetric aldol- and Mannich-type reactions), which behaves like Weinreb amide is also synthesized under similar reaction conditions.
Preparation of Weinreb amides using 4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4- methylmorpholinium chloride (DMT-MM)
Hioki, Kazuhito,Kobayashi, Hiroko,Ohkihara, Rumi,Tani, Shohei,Kunishima, Munetaka
, p. 470 - 472 (2007/10/03)
Weinreb amides were successfully prepared from the corresponding carboxylic acids using 4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chloride (DMT-MM) in the solvents, methanol, isopropyl alcohol, and acetonitrile, which can solubilize DMT-MM
A convenient synthesis of N-methoxy-N-methylamides from carboxylic acids
Sibi,Stessman,Schultz,Christensen,Lu,Marvin
, p. 1255 - 1264 (2007/10/02)
Carboxylic acids can be converted to their corresponding N-methoxy-N-methylamides in high yields using 2-chloro-1-methylpyridinium iodide as the coupling agent. The reaction proceeds without racemization when chiral carboxylic acids are used as the starting material.