776327-02-7

Basic information

• Product Name: methyl (R)-3-amino-2-benzylpropanoate
• Synonyms: methyl (R)-3-amino-2-benzylpropanoate
• CAS NO: 776327-02-7
• Molecular Weight: 193.246
• Mol File: 776327-02-7.mol

Chemical Properties

• CAS DataBase Reference: methyl (R)-3-amino-2-benzylpropanoate(CAS DataBase Reference)
• NIST Chemistry Reference: methyl (R)-3-amino-2-benzylpropanoate(776327-02-7)
• EPA Substance Registry System: methyl (R)-3-amino-2-benzylpropanoate(776327-02-7)

Safety Data

• Hazardous Substances Data: 776327-02-7(Hazardous Substances Data)

Upstream product

• 748127-65-3 methyl 2-[(benzyloxyamino)methyl]-3-phenylpropionate 
• 1404371-21-6 methyl 2-benzyl-3-[(R)-1-phenylethylamino]propanoate 
• 18020-59-2 methyl 3-hydroxy-2-methylidene-3-phenylpropionate 
• 1404370-89-3 methyl (R)-2-benzyl-3-(benzylamino)propanoate 
• 100-52-7 benzaldehyde 
• 124957-36-4 Methyl 3-acetoxy-2-methylene-3-phenylpropanoate 
• 222179-74-0 methyl (E/Z)-2-[(benzylamino)methyl]-3-(phenyl)acrylate 
• 220116-92-7 (2S,5R)-5-Benzyl-2-tert-butyl-4-methoxy-5,6-dihydro-2H-pyrimidine-1-carboxylic acid tert-butyl ester 
• 100-39-0 benzyl bromide 

Downstream Products

• 220117-36-2 methyl 2-benzyl-3-(tert-butoxycarbonylamino)propanoate 
• 1239975-23-5 methyl (R)-(+)-3-acetamido-2-benzylpropanoate 
• 1448639-60-8 (R)-methyl 2-benzyl-3-((S)-3-(tert-butoxycarbonylamino)-4-phenylbutanamido) propanoate 

Relevant articles and documents

Synthesis of chiral β2-amino acids by asymmetric hydrogenation

The synthesis of chiral β2-amino acids by homogeneous asymmetric hydrogenation is discussed. Prochiral β-aryl- or β-hetaryl-α-N-benzyl/N-acetyl/N-Boc substituted α- aminomethylacrylates used as substrates were prepared by a Baylis-Hillman react

A general approach to the synthesis of β2-amino acid derivatives via highly efficient catalytic asymmetric hydrogenation of α-aminomethylacrylates

A new strategy was developed for the synthesis of a valuable class of α-aminomethylacrylates via the Baylis-Hillman reaction of different aldehydes with methyl acrylate followed by acetylation of the resulting allylic alcohols and SN2′-type amination of the allylic acetates. Asymmetric hydrogenation of these diverse olefinic precursors using rhodium(Et-Duphos) catalysts provided the corresponding β2-amino acid derivatives with excellent enantioselectivities and exceedingly high reactivities (up to >99.5% ee and S/C=10,000). The first hydrogenation of (Z)-configurated substrates was studied for the synthesis of β2-amino acid derivatives. The high influence of the substrate geometry and steric hindrance on the reactivity and enantioselectivity was also disclosed for this reaction. This protocol provides a highly practical, facile and scalable method for the preparation of optically pure β2- amino acids and their derivatives under mild reaction conditions.

EPC-synthesis of β-amino acid derivatives through lithiated hydropyrimidines

Racemic and enantiopure 2-tert-butyltetrahydropyrimidinones (from pivalaldehyde and 3-aminocarboxylic acids) are converted to Alloc-, Boc-, and Z-protected cyclic imino esters (7-10, Schemes 2-4). These are deprotonated to Li enaminates (K, L). Reactions with electrophiles (prim., sec. alkyl, allyl, benzyl, propargyl halides, aldehydes, imines, enoates) give good yields and are highly diastereoselective (products 11-42, Schemes 5-10). A two-step cleavage (removal of protecting group and hydrolysis) under very mild conditions converts the heterocyclic products to α-branched β-amino acid methyl esters (43-61, Schemes 11-13). The structure of the products is determined by NMR spectroscopy (Figure 1), by chemical correlation (Scheme 14), and by X-ray analysis (Figure 2, 3, 7, Table 1). A structure of the Li enaminates is proposed (Figure 4). Mechanistic models are derived for the reactions occurring with formation of two stereogenic centers with relative topicity like (Figures 5, 6).