117560-14-2

Basic information

• Product Name: N-[1-(S)-Benzyloxycarbonyl-3-phenylpropyl]-L-alanine tert-Butyl Ester
• Synonyms: N-[1-(S)-Benzyloxycarbonyl-3-phenylpropyl]-L-alanine tert-Butyl Ester
• CAS NO: 117560-14-2
• Molecular Formula: C₂₄H₃₁NO₄
• Molecular Weight: 397.50724
• Product Categories: Amino Acids & Derivatives;Aromatics;Intermediates;Amino Acids & Derivatives, Aromatics, Intermediates
• Mol File: 117560-14-2.mol

Chemical Properties

• Boiling Point: 502.176°C at 760 mmHg
• Flash Point: 257.507°C
• Appearance: /
• Density: 1.09g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.536
• Solubility: Chloroform, Dichloromethane, Ethyl Acetate, Methanol
• CAS DataBase Reference: N-[1-(S)-Benzyloxycarbonyl-3-phenylpropyl]-L-alanine tert-Butyl Ester(CAS DataBase Reference)
• NIST Chemistry Reference: N-[1-(S)-Benzyloxycarbonyl-3-phenylpropyl]-L-alanine tert-Butyl Ester(117560-14-2)
• EPA Substance Registry System: N-[1-(S)-Benzyloxycarbonyl-3-phenylpropyl]-L-alanine tert-Butyl Ester(117560-14-2)

Safety Data

• Hazardous Substances Data: 117560-14-2(Hazardous Substances Data)

Usage

Chemical Properties

Colourless Oil

Uses

Intermediate in the preparation of Imidaprilat

InChI:InChI=1/C24H31NO4/c1-18(22(26)29-24(2,3)4)25-21(16-15-19-11-7-5-8-12-19)23(27)28-17-20-13-9-6-10-14-20/h5-14,18,21,25H,15-17H2,1-4H3/t18-,21?/m0/s1

Upstream product

• 39149-80-9 tert-butyl 2-bromopropionate 
• 117560-24-4 p-tolylsulfonic caid salt of L-homophenylalanine benzyl ester 
• 21691-50-9 Ala-OtBu 
• 112076-94-5 2-trifluoromethanesulfonyloxy-4-phenylbutyric acid benzyl ester 
• 109684-03-9 benzyl 2(R)-hydroxy-4-phenylbutyrate 
• 5440-40-4 2-(acetylamino)-4-phenylbutanoic acid 
• 1012-05-1 D,L-homophenylalanine 
• 100-39-0 benzyl bromide 
• 943-73-7 D-homophenylalanine 
• 16503-46-1 2-bromo-4-phenyl butanoic acid 
• 4263-93-8 2-hydroxy-4-phenylbutanoic acid 

Downstream Products

• 109715-01-7 (R)-3-[(S)-2-((S)-1-Benzyloxycarbonyl-3-phenyl-propylamino)-propionyl]-5-tert-butyl-2,3-dihydro-[1,3,4]thiadiazole-2-carboxylic acid benzyl ester 
• 109683-79-6 Utibaprilat 
• 117560-17-5 (S)-3-[(S)-2-((S)-1-Benzyloxycarbonyl-3-phenyl-propylamino)-propionyl]-2-oxo-imidazolidine-1,4-dicarboxylic acid 1-benzyl ester 4-tert-butyl ester 
• 117560-18-6 (S)-3-[(S)-2-((S)-1-Benzyloxycarbonyl-3-phenyl-propylamino)-propionyl]-2-oxo-imidazolidine-1,4-dicarboxylic acid 1-benzyl ester 4-tert-butyl ester; compound with (Z)-but-2-enedioic acid 
• 89371-86-8 benzyl (4S)-1-n-butyl-3-{(2S)-2-[N-((1S)-1-benzyloxycarbonyl-3-phenylpropyl)amino]propionyl}-2-oxo-imidazolidine-4-carboxylate 
• 89371-87-9 (4S)-1-n-butyl-3-{(2S)-2-[N-((1S)-1-carboxy-3-phenylpropyl)amino]propionyl}-2-oxo-imidazolidine-4-carboxylic acid 
• 117560-10-8 (S)-3-[(S)-2-((S)-1-Carboxy-3-phenyl-propylamino)-propionyl]-2-oxo-imidazolidine-4-carboxylic acid 
• 89460-20-8 tert-butyl (4S)-1-methyl-3-{(2S)-2-[N-((1S)-1-benzyloxycarbonyl-3-phenylpropyl)amino]propionyl}-2-oxo-imidazolidine-4-carboxylate 
• 89371-44-8 (4S)-1-methyl-3-{(2S)-2-[N-((1S)-1-carboxy-3-phenylpropyl)amino]propionyl}-2-oxo-imidazolidine-4-carboxylic acid 
• 117605-21-7 tert-butyl (4S)-3-<(2S)-2-propionyl>-1-methyl-2-oxoimidazolidine-4-carboxylate hydrogen maleate 
• 89371-42-6 (2S)-2-amino>propionic acid 
• 117560-15-3 (S)-2-((S)-1-tert-Butoxycarbonyl-ethylamino)-4-phenyl-butyric acid benzyl ester; compound with (Z)-but-2-enedioic acid 

Relevant articles and documents

Design, synthesis, and physicochemical properties of a novel, conformationally restricted 2,3-dihydro-1,3,4-thiadiazole-containing angiotensin converting enzyme inhibitor which is preferentially eliminated by the biliary route in rats

Two novel series of dihydrothiadiazole ring containing inhibitors of angiotensin converting enzyme have been designed and synthesized. The compounds are highly potent enzyme inhibitors and, as a consequence of conformational restriction, chemically stable with respect to undesirable cyclization reactions. The most interesting compound from this series, 5a (FPL 63547), is the monoethyl ester prodrug of the highly potent ''aminocarboxy'' inhibitor 5b (FPL 63674). It produces an antihypertensive effect of long duration in animal models after oral dosing. Unlike other ACE inhibitors, 5b is eliminated almost entirely by biliary clearance in the rat. The favorable pharmacological properties of 5a and 5b are rationalized in terms of their unique physicochemical profiles. The clear preference for biliary clearance seen with 5b is consistent with its lipophilicity and its high degree of net ionization at physiological pH, which results from the very low pK(a) of the C-terminus carboxylic acid function. FPL 63547 is presently undergoing clinical investigation in man.

Studies on Angiotensin Converting Enzyme Inhibitors. 4. Synthesis and Angiotensin Converting Enzyme Inhibitory Activities of 3-Acyl-1-alkyl-2-oxoimidazolidine-4-carboxylic Acid Derivatives

(4S)-1-Alkyl-3-acyl>-2-oxoimidazolidine-4-carboxylic acid derivatives (3) were prepared by two methods.Their angiotensin converting enzyme (ACE) inhibitory activities and antihypertensive effects were evaluated, and the structure-activity relationships were discussed.The dicarboxylic acids 3a-n possessing S,S,S configuration showed potent in vitro ACE inhibitory activities with IC 50 values of 1.1x10-8-1.5x10-9 M.The most potent compound in this series, monoester 3p, had an ID 50 value of 0.24 mg/kg, po for inhibition of angiotensin I induced pressor response in normotensive rats and produced a dose-dependent decrease in systolic blood pressure of spontaneously hypertensive rats (SHRs) at doses of 1-10 mg/kg, po.