82586-62-7Relevant academic research and scientific papers
Continuous Flow Synthesis of ACE Inhibitors From N-Substituted l-Alanine Derivatives
Breen, Christopher P.,Jamison, Timothy F.
supporting information, p. 14527 - 14531 (2019/11/03)
A strategy for the continuous flow synthesis of angiotensin converting enzyme (ACE) inhibitors is described. An optimization effort guided by in situ IR analysis resulted in a general amide coupling approach facilitated by N-carboxyanhydride (NCA) activation that was further characterized by reaction kinetics analysis in batch. The three-step continuous process was demonstrated by synthesizing 8 different ACE inhibitors in up to 88 % yield with throughputs in the range of ≈0.5 g h?1, all while avoiding both isolation of reactive intermediates and process intensive reaction conditions. The process was further developed by preparing enalapril, a World Health Organization (WHO) essential medicine, in an industrially relevant flow platform that scaled throughput to ≈1 g h?1.
An organogel formed from a cyclic β-aminoalcohol
Kang, Chuanqing,Bian, Zheng,He, Yabing,Han, Fushe,Qiu, Xuepeng,Gao, Lianxun
, p. 10746 - 10748 (2011/11/29)
A new organogelator with unique structural feature of a cyclic β-aminoalcohol is presented as the first example of gelation by aminoalcohol through hydrogen-bonding between hydroxy and amine.
Preparation of chiral 1,2,3,4-tetrahydro-6,7-dialkoxy-3-isoquinolinecarboxylic acid and derivatives
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Page/Page column 11, (2008/06/13)
The present invention relates to a process for the production of (S)-1,2,3,4-tetrahydro-6,7-dialkoxy-3-isoquinolinecarboxylic acid compounds (1) and their derivatives from Levodopa (L-Dopa). The ultimately prepared compounds are used as intermediates for, but not limited to, the preparation of substituted derivatives of 1,2,3,4-tetrahydro-6,7-dialkoxy-3-isoquinolinecarboxylic acid wherein R1is hydrogen, lower alkyl, C2-C12 acyl, or R1O together are methylenedioxy; R2is hydrogen, alkyl, substituted alkyl, alkenyl, substituted alkenyl, aryl, substituted aryl, aralkyl or substituted aralkyl group; and R3is hydrogen, C2-C12 acyl group, benzyl, alkoxylcarbonyl group, or aralkoxyl carbonyl group.
PREPARATION OF CHIRAL 1,2,3,4-TETRAHYDRO-6,7-DIALKOXY-3-ISOQUINOLINECARBOXYLIC ACID AND DERIVATIVES BY REACTING LEVODOPA WITH FORMALDEHYDE OR FORMALDEHYDE PRECURSORS
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Page 16, (2010/02/04)
A process for preparation of (S)-1,2,3,4-tetrahydro-6,7-dialkoxy-3-isoquinolinecarboxylic acid compounds and their derivatives of the formula (1) the process compring: (i) reacting Levodopa of formula (2) with formaldehyde or formaldehyde precursors to obtain (S)-1,2,3,4-tetrahydro-6,7-dihydroxy-3-isoquinolinecarboxylic acid of formula (3); (ii) protecting the amino group of formula (3); (iii) alkylating the phenol groups of formula (4) to form compound of formula (5); and (iv) esterifying the carcoxylic acid of formula (5) and optionally removing N-protecting group wherein R1 is hydrogen, lower alkyl, C2-C12 acyl, or R1O together are methylenedioxy; R2 is hydrogen, alkyl, substituted alkyl, alkenyl, substituted alkenyl, aryl, substituted aryl, aralkyl or substituted aralkyl group; R3 is hydrogen, C2-C12 acyl group, benzyl, alkoxylcarbonyl group, or aralkoxyl carbonyl group; wherein P is the protecting group selected from alkoxycarbonyl, acyl, alkyl, aryl, siryl, sulfenyl and sulfonyl.
