1205-02-3

Basic information

• Product Name: N-BENZOYL-DL-ALANINE
• Synonyms: 2-(BENZOYLAMINO)PROPANOIC ACID;BENZOYL-DL-ALANINE;DL-N-BENZOYLALANINE;BZ-DL-ALA-OH;IFLAB-BB F1924-0021;Benzoylalanine;DL-N-BENZOYL-ALPHA-ALANINE;DL-Benzoylalanine
• CAS NO: 1205-02-3
• Molecular Formula: C10H11NO3
• Molecular Weight: 193.2
• EINECS: 214-879-5
• Mol File: 1205-02-3.mol

Chemical Properties

• Melting Point: 165-167°C
• Boiling Point: 329.41°C (rough estimate)
• Flash Point: 227.4 °C
• Appearance: White crystal
• Density: 1.2307 (rough estimate)
• Vapor Pressure: 5.7E-09mmHg at 25°C
• Refractive Index: 1.5300 (estimate)
• Storage Temp.: −20°C
• PKA: 3.86±0.10(Predicted)
• Water Solubility: Very slightly soluble in water.
• BRN: 3201778
• CAS DataBase Reference: N-BENZOYL-DL-ALANINE(CAS DataBase Reference)
• NIST Chemistry Reference: N-BENZOYL-DL-ALANINE(1205-02-3)
• EPA Substance Registry System: N-BENZOYL-DL-ALANINE(1205-02-3)

Safety Data

• WGK Germany: 3
• TSCA: Yes
• HazardClass: IRRITANT
• Hazardous Substances Data: 1205-02-3(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
N-BENZOYL-DL-ALANINE is used as a pharmaceutical intermediate for the synthesis of various drugs and medications. Its unique structure allows it to be a key component in the development of new pharmaceutical compounds, contributing to the advancement of medical treatments and therapies.
As a pharmaceutical intermediate, N-BENZOYL-DL-ALANINE is utilized in the production of drugs that target specific health conditions and diseases. Its role in the pharmaceutical industry is crucial, as it helps in the development of new and effective medications that can improve the quality of life for patients.

Synthesis Reference(s)

Tetrahedron Letters, 17, p. 2205, 1976 DOI: 10.1016/0040-4039(76)80029-9

InChI:InChI=1/C10H11NO3/c1-7(10(13)14)11-9(12)8-5-3-2-4-6-8/h2-7H,1H3,(H,11,12)(H,13,14)/t7-/m0/s1

Upstream product

• 302-72-7 rac-Ala-OH 
• 98-88-4 benzoyl chloride 
• 4774-76-9 N-benzoyl-alanine trimethylsilanyl ester 
• 14839-73-7 2-<α-Anilino-isobutyrylamino>-propionsaeure-anilid 
• 51127-13-0 2-phenyl-4-methyl-4H-oxazolin-5-one 
• 7244-67-9 methyl N-benzoylalaninate 
• 7732-18-5 water 
• 64-17-5 ethanol 
• 4452-17-9 N-benzoyl-α,β-dehydroalanine 
• 623-11-0 1-methyl-4-nitrosobenzene 
• 2584-86-3 N-thiobenzoyl-DL-alanine 
• 7722-84-1 dihydrogen peroxide 
• 959-22-8 p-nitrophenylbenzoate 
• 138079-74-0 C₁₂H₁₃NO₄S 

Downstream Products

• 7244-67-9 methyl N-benzoylalaninate 
• 115245-46-0 N-(1-methoxyethyl)benzamide 
• 4774-76-9 N-benzoyl-alanine trimethylsilanyl ester 
• 31120-55-5 N-(1-benzoyl-3,5-dimethyl-2,4-dioxo-pyrrolidin-3-yl)-benzamide 
• 100969-24-2 N-(1-methyl-2-oxo-2-[4]pyridyl-ethyl)-benzamide 
• 93732-93-5 N-(1-methyl-2-oxo-2-[3]pyridyl-ethyl)-benzamide 
• 111034-07-2 N-(N-benzoyl-L-alanyl)-N'-o-toluoyl-hydrazine 
• 111034-08-3 N-(N-benzoyl-L-alanyl)-N'-m-toluoyl-hydrazine 
• 6304-98-9 (S)-N-benzoyl-alanine anilide 
• 17966-60-8 D-N-benzoylalanine 
• 2198-64-3 N-benzoyl-L-alanine 
• 114006-16-5 N-(N-benzoyl-L-alanyl)-N'-(3-nitro-benzoyl)-hydrazine 
• 6304-98-9 N-(1-(phenylcarbamoyl)ethyl)benzamide 
• 1192-72-9 4,5-dimethylimidazole-2(3H)-thione 

Relevant articles and documents

Cu(II)-promoted oxidative C-N bond cleavage of N-benzoylamino acids to primary aryl amides

A novel protocol for CuCl2-promoted oxidative C-N bond cleavage of N-benzoyl amino acids was developed. It is the first example of using accessible amino acid as an ammonia synthetic equivalent for the synthesis of primary aryl amides via CuCl2-promoted oxidative C-N bond cleavage reaction. The present protocol shows excellent functional group tolerance and provides an alternative method for the synthetic of primary aryl amides in 84-96% yields.

Palladium-Catalyzed Allenamide Carbopalladation/Allylation with Active Methine Compounds

A palladium-catalyzed allenamide carbopalladation/allylation with active methine compounds has been developed. Various indoles and isoquinolinones bearing a quaternary carbon center were achieved with good efficiency, a broad substrate scope and good functional group tolerance. This reaction underwent cascade oxidative addition, carbopalladation, and allylic alkylation, and two new C-C bonds were formed in one pot.

Nickel-Catalyzed Multicomponent Coupling: Synthesis of α-Chiral Ketones by Reductive Hydrocarbonylation of Alkenes

A nickel-catalyzed, multicomponent regio- and enantioselective coupling via sequential hydroformylation and carbonylation from readily available starting materials has been developed. This modular multicomponent hydrofunctionalization strategy enables the straightforward reductive hydrocarbonylation of a broad range of unactivated alkenes to produce a wide variety of unsymmetrical dialkyl ketones bearing a functionalized α-stereocenter, including enantioenriched chiral α-aryl ketones and α-amino ketones. It uses chiral bisoxazoline as a ligand, silane as a reductant, chloroformate as a safe CO source, and a racemic secondary benzyl chloride or an N-hydroxyphthalimide (NHP) ester of a protected α-amino acid as the alkylation reagent. The benign nature of this process renders this method suitable for late-stage functionalization of complex molecules.

Organocatalytic asymmetric [4+2] cyclization of 2-benzothiazolimines with azlactones: Access to chiral benzothiazolopyrimidine derivatives

An organocatalytic asymmetric domino Mannich/cyclization reaction between 2-benzothiazolimines with azlactones has been successfully developed. With the bifunctional squaramide catalyst, this formal [4+2] cyclization occurs with good to high yields and excellent stereoselectivities (up to 99% ee, >20?:?1 dr), providing an efficient and mild access to chiral benzothiazolopyrimidines bearing adjacent tertiary and quaternary stereogenic centers.

Asymmetric construction of dihydrobenzofuran-2,5-dione derivatives via desymmetrization of p-quinols with azlactones

The desymmetrization of p-quinols through a chiral bisguanidinium hemisalt catalyzed enantioselective Michael addition/lactonization cascade reaction with azlactones was reported. 3-Amino-benzofuran-2,5-diones containing a chiral amino acid residue were achieved with up to 99% ee and >19?:?1 dr. An exploration of the structure of the catalyst bisguanidinium was undertaken, revealing a bifunctional catalytic model.

METHODS OF TREATING OR PREVENTING COGNITIVE IMPAIRMENT USING INDANE ACETIC ACID DERIVATIVES BASED ON APOE4 GENOTYPE

The present invention provides indane acetic acid and their derivatives and methods for the treating and/or preventing of cognitive disorders based on the ApoE4 genotype of human subjects.

METHODS OF DOSE ADMINISTRATION FOR TREATING OR PREVENTING COGNITIVE IMPAIRMENT USING INDANE ACETIC ACID DERIVATIVES

The present invention provides indane acetic acid and their derivatives and methods for the treating and/or preventing of cognitive disorders.

Reactivity of α-Amino Acids in the Reaction with Esters in Aqueous–1,4-Dioxane Media

The kinetics of the reaction of a series of α-amino acids with 4-nitrophenyl acetate, 4-nitrophenyl benzoate, and 2,4,6-trinitrophenyl benzoate in aqueous 1,4-dioxane medium has been studied. Kinetics of the reactions involving 4-nitrophenyl acetate and 2,4,6-trinitrophenyl benzoate has complied with the Br?nsted dependence and revealed linear correlation between rate constant logarithm and the energy difference of the frontier orbitals of α-amino acids anions.

Synthesis of an enantiopure thioester as key substrate for screening the sensitivity of penicillin binding proteins to inhibitors

The synthesis of the enantiopure thioester (R)-2-(2-benzamidopropanoylthio)acetic acid was developed. After the exploration of several activation methods, reaction conditions were found for the formation of the thioester bond in the presence of propylphosphonic anhydride with high enantioselectivity (ee > 99%). The thioester activity of Penicillin Binding Proteins is helpful in research programs looking for new lead structures to overcome the problem of bacterial resistance.

Regiodivergent Enantioselective γ-Additions of Oxazolones to 2,3-Butadienoates Catalyzed by Phosphines: Synthesis of α,α-Disubstituted α-Amino Acids and N,O-Acetal Derivatives

Phosphine-catalyzed regiodivergent enantioselective C-2- and C-4-selective γ-additions of oxazolones to 2,3-butadienoates have been developed. The C-4-selective γ-addition of oxazolones occurred in a highly enantioselective manner when 2-aryl-4-alkyloxazol-5-(4H)-ones were employed as pronucleophiles. With the employment of 2-alkyl-4-aryloxazol-5-(4H)-ones as the donor, C-2-selective γ-addition of oxazolones took place in a highly enantioselective manner. The C-4-selective adducts provided rapid access to optically enriched α,α-disubstituted α-amino acid derivatives, and the C-2-selective products led to facile synthesis of chiral N,O-acetals and γ-lactols. Theoretical studies via DFT calculations suggested that the origin of the observed regioselectivity was due to the distortion energy that resulted from the interaction between the nucleophilic oxazolide and the electrophilic phosphonium intermediate.