88767-98-0

Usage

Uses

Used in Pharmaceutical Industry:
Ethyl (R)-4-phenyl-2-[[(trifluoromethyl)sulfonyl]oxy]butyrate is used as a key intermediate in the synthesis of Enalapril-d3 Hydrochloride (E555258). Ethyl (R)-4-phenyl-2-[[(trifluoromethyl)sulfonyl]oxy]butyrate is the hydrochloride salt of Enalapril-d3 (E555253), which is a labeled version of Enalapril (E555403). Enalapril is an antihypertensive drug that functions as an angiotensin-converting enzyme (ACE) inhibitor, playing a crucial role in the treatment of hypertension and heart failure.
In the synthesis process, Ethyl (R)-4-phenyl-2-[[(trifluoromethyl)sulfonyl]oxy]butyrate contributes to the formation of the desired active pharmaceutical ingredient (API) by undergoing a series of chemical reactions. Its presence in the synthesis pathway highlights its importance in the development of effective medications for cardiovascular diseases.
Furthermore, the use of Ethyl (R)-4-phenyl-2-[[(trifluoromethyl)sulfonyl]oxy]butyrate in the synthesis of Enalapril-d3 Hydrochloride also underscores its potential in the production of isotopically labeled compounds. These labeled compounds are valuable tools in research and development, as they can be used to study the metabolism, pharmacokinetics, and mechanism of action of the parent drug, Enalapril, in various biological systems. This information is crucial for optimizing drug design and improving therapeutic outcomes.

InChI:InChI=1/C13H15F3O5S/c1-2-20-12(17)11(21-22(18,19)13(14,15)16)9-8-10-6-4-3-5-7-10/h3-7,11H,2,8-9H2,1H3/t11-/m1/s1

Upstream product

• 1914-59-6 (E)-2-oxo-4-phenyl-3-butenoic acid 
• 110143-65-2 2-oxo-4-phenylbut-3-enoic acid 2-isopropyl-5-methylcyclohexyl ester 
• 29678-81-7 (R)-2-hydroxy4-phenylbutanoic acid 
• 110143-66-3 R-2-hydroxy-4-phenylbutyric acid L-menthyl ester 
• 358-23-6 trifluoromethylsulfonic anhydride 
• 90315-82-5 ethyl (R)-2-hydroxy-4-phenylbutyrate 

Downstream Products

• 82717-95-1 Benzyl (2S)-2-amino>propionate 
• 106860-19-9 (1S,9S)-t-butyl 9-<(1S)-ethoxycarbonyl-3-phenylpropylamino>octahydro-10-oxo-6H-pyridazino<1,2-a><1,2>diazepine-1-carboxylate 
• 140677-50-5 (3S,1'S)-ethyl-3-((1-(ethoxycarbonyl)-3-phenylpropyl)amino)-2-oxo-2,3,4,5-tetrahydro-1H-pyrrolo<1,2-b><1,2>diazepine-1-acetate 
• 110221-32-4 (S)-2-((2R,6R)-5-Oxo-2-thiophen-2-yl-[1,4]thiazepan-6-ylamino)-4-phenyl-butyric acid ethyl ester 
• 148530-36-3 (3R,1'S)-Ethyl 3-<(1-ethoxycarbonyl-3-phenylpropyl)amino>-4-oxo-2,3,4,5-tetrahydropyrrolo<2,1-b><1,3,4>thiadiazepine-5-acetate 
• 110143-57-2 (S)-2-((2S,6R)-5-Oxo-2-thiophen-2-yl-[1,4]thiazepan-6-ylamino)-4-phenyl-butyric acid ethyl ester 
• 110221-31-3 (S)-2-((2S,6R)-5-Oxo-2-phenyl-[1,4]thiazepan-6-ylamino)-4-phenyl-butyric acid ethyl ester 
• 110143-56-1 (2R,6R)-6-<<(S)-1-(ethoxycarbonyl)-3-phenylpropyl>amino>-2-phenylperhydro-1,4-thiazepin-5-one 
• 110221-33-5 (S)-2-((2S,6R)-5-Oxo-2-thiophen-3-yl-[1,4]thiazepan-6-ylamino)-4-phenyl-butyric acid ethyl ester 
• 110143-58-3 (S)-2-((2R,6R)-5-Oxo-2-thiophen-3-yl-[1,4]thiazepan-6-ylamino)-4-phenyl-butyric acid ethyl ester 
• 110267-58-8 (S)-2-((3R,6R)-5-Oxo-3-phenyl-[1,4]thiazepan-6-ylamino)-4-phenyl-butyric acid ethyl ester 
• 110143-59-4 (S)-2-((3S,6R)-5-Oxo-3-phenyl-[1,4]thiazepan-6-ylamino)-4-phenyl-butyric acid ethyl ester 
• 102208-46-8 tert-butyl α-<(3S,6R)-6-<<(S)-1-(ethoxycarbonyl)-3-phenylpropyl>amino>-5-oxo-3-(2-thienyl)perhydro-1,4-thiazepin-4-yl>acetate 
• 150849-84-6 (S)-3-butyl-6-(2-phenylethyl)-4H-1,2,4-oxadiazin-5(6H)-one 

Relevant academic research and scientific papers

LIPOPHILIC MACROCYCLIC LIGANDS, COMPLEXES THEREOF, AND USES OF SAME

The present invention relates to novel lipophilic macrocyclic ligands, the complexes thereof, in particular radioactive complexes, and the uses of same in medical imaging and/or in therapy, in particular in interventional radiology.

ENALAPRIL-NITROXYDERIVATIVES DERIVATIVES AND RELATED COMPOUNDS AS ACE INHIBITORS FOR THE TREATMENT OF CARDIOVASCULAR DISEASES

Compounds of formula (I): A-(X1-ONO2)S wherein A is a known ACE-inhibitor such as enalapril and X1 is a spacer such as a (C1-C6)-alkylene. The complete definition of A and X1 is given in claim 1. The compounds can be used as ACE-inhibitors for the treatment of cardiovascular and renal diseases and inflammatory processes. The example of formula (1) has an improved pharmacological activity when compared with the structurally closest related prior art compound.

SYNTHESIS OF N-ALKYL-1,2,4-OXADIAZINONES AS ANGIOTENSIN-II (AT1) RECEPTOR ANTAGONISTS

4-Alkyl-1,2,4-oxadiazinones were prepared by regiospecific alkylation of the corresponding 4H-oxadiazinones, which were synthesized by a trimethylaluminium mediated cyclization reaction.Alkylation was regiospecyfic and generally facile; in one example, however, an unusual fragmentation reaction occurred.A homochiral oxadiazineone was also prepared and alkylated under the described conditions. 4-Biphenylmethyl-1,2,4-oxadi-azinones were potent angiotensin-II receptor antagonists.

Angiotensin-Converting Enzyme Inhibitors: Perhydro-1,4-thiazepin-5-one Derivatives

α-amino>-5-oxoperhydro-1,4-thiazepin-4-yl>acetic acids (monoester monoacids) and their dicarboxylic acids having the hydrophobic substituents at the 2- or 3-position of the thiazepinone ring were prepared and assayed for angiotensin-converting enzyme (ACE) inhibitory activity.The dicarboxylic acids having the pseudoequatorial amino groups at the 6-position and the pseudoequatorial hydrophobic substituents at the 2- or 3-position of the chair conformation of the thiazepinone ring had potent in vitro inhibitory activity.The monoester monoacids having the hydrophobic substituents at the 2-position suppressed pressor response to angiotensin I for a longer duration than those having the substituents at the 3-position when administered orally.The structure-activity relationship was studied by conformational energy calculations of the thiazepinone ring.

The Design and Synthesis of the Angiotensin Converting Enzyme Inhibitor Cilazapril and Related Bicyclic Compounds

The postulated binding functions for the active site of Angiotensin Converting Enzyme (A.C.E.), derived in an earlier study, have made possible the design of improved inhibitors.Consequently, (1S,9S)-9-octahydro-10-oxo-6H-pyridazodiazepine-1-carboxylic acid (Cilazapril), and related compounds, have been synthesized.They are very active inhibitors of A.C.E. and are highly potent antihypertensives in vivo.

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.