Preparation method of N-[1-(S)-ethoxy carbonyl-3-phenyl propyl]-L-alanine
The invention provides a preparation method of N-[1-(S)-ethoxy carbonyl-3-phenyl propyl]-L-alanine. The preparation method comprises the following steps: performing addition reaction on a compound I and a compound II under the action of a first catalyst to obtain an addition product, wherein the first catalyst is selected from a first thiourea compound and/or a urea compound; performing hydrogenation reaction on the addition product to obtain the N-[1-(S)-ethoxy carbonyl-3-phenyl propyl]-L-alanine. The first catalyst (the first thiourea compound and/or the urea compound) can be added to the reaction system, the selectivity of the addition reaction is improved and the separation efficiency of the required product in the addition reaction process is improved, so that the yield of the final product N-[1-(S)-ethoxy carbonyl-3-phenyl propyl]-L-alanine is increased. The method has the advantages of being short in synthesis route, simple in aftertreatment, capable of being applied to industrialized production and the like.
N-(4-oxo-butanoic acid) -L-amino acid-ester derivatives and methods of preparation thereof
The present invention provides a compound of the following formula (I): wherein R1 is methyl or 4-aminobutyl, which may be acylated; X is phenyl or substituted phenyl; W is an esterified group removable by hydrogenolysis. Also disclosed is the preparation method and the application of formula (I) compound.
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Page/Page column 4
(2010/02/15)
Addition of enantiomerically pure amines to activated olefines II. On the addition to ethyl (E)-4-oxo-4-phenyl-2-butenoate
The addition of (S)-phenethylamine to ethyl (E)-4-oxo-4-phenyl-2-butenoate shows no kinetic selectivity, whereas - according to the b,pl,H-rule the AB-and BB-product are kinetically preferred in the addition of (S)-alanine-isopropylester and -benzylester,
Knollmüller, Max,Ferencic, Mathias,G?rtner, Peter,Girreser, Ulrich,Klinge, Michael,Gaischin, Larissa,Mereiter, Kurt,Noe, Christian R.
p. 769 - 782
(2007/10/03)
Synthesis of a highly active angiotensin converting enzyme inhibitor: 2-[N-[(S)-1-ethoxycarbonyl-3-phenylpropyl]-L-alanyl]-(1S,3S,5S)-2-azabicyc lo[3.3.0]octane-3-carboxylic acid (Hoe 498)
The convergent, diastereoselective synthesis of 2-[N-[(S)-1-ethoxycarbonyl-3-phenylpropyl]-L-alanyl]-(1S,3S,5S)-2-azabicyc lo[3.3.0]octane-3-carboxylic acid (Hoe 498), a new ACE-inhibitor with improved bioavailability and pharmacokinetics, is described.
Teetz,Geiger,Henning,Urbach
p. 1399 - 1401
(2007/10/02)
A FAVOURABLE DIASTEREOSELECTIVE SYNTHESIS OF N-(1-S-ETHOXYCARBONYL-3-PHENYLPROPYL)-S-ALANINE
N-(1-S-Ethoxycarbonyl-3-phenylpropyl)-S-alanine is prepared by Michael addition of S-alaninebenzylester to ethyl-4-oxo-4-phenyl-2-butenoate in a regio- and diastereoselective fashion and subsequent catalytic hydrogenolysis.
Urbach, H.,Henning, R.
p. 1143 - 1146
(2007/10/02)
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