Saari, Walfred S.; Fischer, Thorsten E. published an article in Synthesis. The title of the article was 《A convenient and versatile synthesis of chiral aliphatic and allylic amines》.Application of 87694-50-6 The author mentioned the following in the article:
Treating (S)- and (R)-Boc-Leu-OH in EtOH containing N-methylmorpholine with ClCO2CH2CHMe2 and then with MeONHMe gave 89-99% (S)- and (R)-Boc-Leu-NMeOMe, which were reduced with LiAlH4 in THF to give 69-72% Boc-Leu-H. Wittig reaction of these aldehydes with Ph3P+CH2R Br- (R = Me, Et, Pr, Bu) and KN(SiMe3)2 in THF-PhMe gave 6 (S)- and (R)-Me2CHCH2CH(NHBoc)CH:CHR-Z [(R)-I] in 72-97% yield. I in EtOH were hydrogenated over Pd/C to give 86-99% (S)- and (R)-Me2CHCH2CH(NHBoc)CH2CH2R [(R)-II]. Deprotection of (S)-I (R = Pr) and all 6 II with dry HCl in EtOAc gave 46-93% title amine hydrochlorides. In the part of experimental materials, we found many familiar compounds, such as (S)-N-Methyl-N-methoxy-2-(tert-butoxycarbonylamino)-4-methylpentanamide(cas: 87694-50-6Application of 87694-50-6)
(S)-N-Methyl-N-methoxy-2-(tert-butoxycarbonylamino)-4-methylpentanamide(cas: 87694-50-6) belongs to amides. Because of the greater electronegativity of oxygen, the carbonyl (C=O) is a stronger dipole than the N–C dipole. The presence of a C=O dipole and, to a lesser extent a N–C dipole, allows amides to act as H-bond acceptors.Application of 87694-50-6 In primary and secondary amides, the presence of N–H dipoles allows amides to function as H-bond donors as well.
Referemce:
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics