28875-17-4

Basic information

• Product Name: BOC-L-ALANINE METHYL ESTER
• Synonyms: L-Alanine methyl ester, N-BOC protected;Methyl (2S)-2-[(tert-butoxycarbonyl)amino]propanoate;Methyl (S)-2-(tert-butoxycarbonylamino)propanoate;(S)-Methyl 2-(tert-butoxycarbonylaMino)propanoate;N-Boc-L-alanine Methyl ester, 95%;Methyl N-(tert-butoxycarbonyl)-L-alaninate;BOC-L-Ala-Methyl ester;Boc-L-Ala-OMe
• CAS NO: 28875-17-4
• Molecular Formula: C₉H₁₇NO₄
• Molecular Weight: 203.24
• EINECS: 1533716-785-6
• Mol File: 28875-17-4.mol

Chemical Properties

• Melting Point: 32-35 °C(lit.)
• Boiling Point: 278℃
• Flash Point: >230 °F
• Appearance: White/Powder
• Density: 1.03 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.004mmHg at 25°C
• Refractive Index: 1.4315 (estimate)
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• PKA: 11.21±0.46(Predicted)
• BRN: 1872545
• CAS DataBase Reference: BOC-L-ALANINE METHYL ESTER(CAS DataBase Reference)
• NIST Chemistry Reference: BOC-L-ALANINE METHYL ESTER(28875-17-4)
• EPA Substance Registry System: BOC-L-ALANINE METHYL ESTER(28875-17-4)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 28875-17-4(Hazardous Substances Data)

Usage

Uses

Used in Organic Chemistry:
BOC-L-ALANINE METHYL ESTER is used as a reagent for the synthesis of peptides and other organic molecules, facilitating the selective reactions of functional groups in synthetic processes.
Used in Peptide Synthesis:
BOC-L-ALANINE METHYL ESTER is used as a protecting group for the amino group, ensuring that the amine functionality of the alanine molecule is safeguarded during the synthesis process, which is vital for the successful formation of peptide bonds.
Used in Pharmaceutical Production:
BOC-L-ALANINE METHYL ESTER is used as a building block in the production of bioactive compounds and pharmaceuticals, contributing to the development of new drugs and therapeutic agents.
Used in Biotechnological Applications:
BOC-L-ALANINE METHYL ESTER is used in the biotechnology industry for the creation of materials with specific properties, such as those required for medical or industrial uses, leveraging its role in the synthesis of complex organic molecules.

InChI:InChI=1/C9H17NO4/c1-6(7(11)13-5)10-8(12)14-9(2,3)4/h6H,1-5H3,(H,10,12)/t6-/m0/s1

Upstream product

• 19578-68-8 4-(4-benzyloxyphenyl) iodide 
• 93267-04-0 N-(tert-butoxycarbonyl)-L-3-iodoalanine methyl ester 
• 2899-57-2 Sphenyl N-benzyloxycarbonylaminoethanothioate 
• 100-36-7 N,N-diethylethylenediamine 
• 395647-18-4 N-{3-[(N,N-dimethylaminophenyl)-4'-diazenyl]benzoyl}-N-tert-butyloxycarbonylalanine methyl ester 

Downstream Products

• 15761-38-3 L-N-Boc-Ala 
• 2491-20-5 L-alanine methyl ester hydrochloride 
• 93371-30-3 tert-butyl [(2S)-4-chloro-3-oxobutan-2-yl]carbamate 
• 196819-41-7 (S)-5-[1-(tert-butoxycarbonyl)aminoethyl]oxazole 
• 310450-35-2 (3S,R_S)-N-(tert-butoxycarbonyl)-3-amino-1-(p-tolylsulfinyl)-2-butanone 
• 142723-69-1 [L-(trans)]-4-[(t-butoxycarbonyl)amino]-2-pentenoic acid 
• 157394-45-1 (2S,3S)-N-(tert-butoxycarbonyl)-3-amino-2-butanol 
• 207924-92-3 (4S)-4-[(tert-butoxycarbonyl)amino]pentanoic acid 
• 157394-46-2 (2R,3S)-N-(tert-butoxycarbonyl)-3-amino-2-butanol 
• 310450-40-9 (2R,3S,R_S)-N-(tert-butoxycarbonyl)-3-amino-1-(p-tolylsulfinyl)-2-butanol 
• 310450-37-4 (2S,3S,R_S)-N-(tert-butoxycarbonyl)-3-amino-1-(p-tolylsulfinyl)-2-butanol 
• 499783-29-8 (Z)-(3S)-3-(tert-butoxycarbanylamino)-1-(4'-tolylthio)-1-nitrobut-1-ene 
• 499783-28-7 ((S)-2-Hydroxy-1-methyl-3-nitro-3-p-tolylsulfanyl-propyl)-carbamic acid tert-butyl ester 
• 16112-59-7 4-methyl-2-oxazolidone 

Relevant articles and documents

Development of a temporary marker for peptides

3-[(N,N-Dimethylaminophenyl)-4′-diazenyl]benzoic acid was coupled with several amino acid esters and the product acylated further with Boc. The material thus obtained was then submitted to cleavage by electrolysis and nucleophilic attack in order to evaluate the possibility of using this chromophore as a temporary marker.

A temporary marker for biological applications

Having in mind the development of new colour labelled amino acid derivatives, a carboxyl azo dye was coupled to amino acid esters to give the corresponding orange N-acyl derivatives, which were in turn further acylated at their N-terminus with Boc for investigation of the conditions of possible cleavage of the chromophore by electrolysis or with nucleophiles. While difficulties were met with electrolysis owing to competitive reduction of the azo group, cleavage with N,N-diethylaminoethylamine (DEAEA) gave satisfactory results. This allows the use of the chromophore as a temporary marker.

Synthesis of a 3-aminopiperidin-2,5-dione as a conformationally constrained surrogate of the Ala-Gly dipeptide

The preparation of the Boc-{Ala-Gly}-OBn pseudopeptide 4 is reported. The key intermediate, aminoester 5b, was obtained by a cross-coupling reaction of alaninezinc iodide 6 and the thioester of glycine 9.

An efficient synthesis of [ring-14C]-L-tyrosine from [U-14C ]-phenol

The title compound was prepared in good overall yield and high enantiopurity via a five step route beginning with [U-14C]-phenol, 4. Benzyl ether 5 was prepared from 4 under standard conditions and underwent selective iodination at the 4-position in the presence of iodine and mercuric oxide. Palladium catalysed cross coupling of the resulting aryl iodide 6 and the organozinc intermediate derived from N-tert-butoxycarbonyl-3-iodo-alanine methyl ester, 7, proceeded smoothly to give 8. Debenzylation and acid hydrolysis afforded the deprotected amino acid as the hydrochloride salt. Purification (flash chromatography) was necessary in only two of the five steps in the synthesis.