79219-15-1

Upstream product

• 79821-79-7 N-(ethoxycarbonyl)-L-alanine acid chloride 
• 71-43-2 benzene 
• 16639-86-4 N-ethoxycarbonyl-L-alanine 
• 89312-80-1 ethyl (1-(methoxy(methyl)amino)-1-oxopropan-2-yl)carbamate 

Downstream Products

• 114550-56-0 (3S,4S)-4-((ethoxycarbonyl)amino)-2,3-diphenyl-1-penten-3-ol 
• 299-42-3 ephedrine 
• 90-82-4 pseudoephedrine 
• 26343-76-0 (S)-(-)-2-ethoxycarbonylamino-1-phenylpropane 
• 79297-22-6 ((1S,2S)-2-Hydroxy-1-methyl-2-phenyl-ethyl)-carbamic acid ethyl ester 
• 79297-23-7 (1R,2S)-2-<(ethoxycarbonyl)amino>-1-phenyl-1-propanol 
• 1462-73-3 (S)-(+)-amphetamine hydrochloride 
• 16251-45-9 (4S,5R)-4-methyl-5-phenyl-oxazolidin-2-one 
• 114550-59-3 (-)-(4S,5S)-3,4-dimethyl-5-phenyl-5-(1-phenylethenyl)oxazolidine 
• 114550-58-2 (4S,5S)-4-methyl-5-phenyl-5-(1-phenylethenyl)oxazolidine 
• 114550-57-1 (3S,4S)-4-amino-2,3-diphenyl-1-penten-3-ol 

Relevant academic research and scientific papers

Synthesis of [14C]CI-980, ethyl [5-amino-1,2-dihydro-2(S)-methyl-3-[14C]phenylpyrido[3,4-b]pyrazin-7 -yl]carbamate isethionate salt, a tubulin-binding, antimitotic, broad-spectrum antitumor agent

[14C]CI-980 (14b) was synthesized in eight steps starting from [U-14C]benzene (5), which was converted to bromo[14C]benzene (6) in the presence of tetrabutylammonium bromide as catalyst. Reaction of 6 with the anion of N-ethoxycarbonyl-N'-methoxy-N'-methyl-L-alaninamide (4a) gave the chiral (S)-ketone 8 with ee exceeding 96%. Sodium borohydride reduction of 8, followed by sequential condensation with ethyl 6-amino-4-chloro-4-nitro-2-pyridine carbamate (11), chromium trioxide oxidation, and catalytic hydrogenation over Raney nickel gave the free base form of [14C]CI-980 (14a), which was extremely unstable and readily aromatized to 15. The free base 14a was, however, isolated under specially developed conditions and converted to the crystalline isethionate salt 14b in pure form.

Zinc borohydride reduction of α-amino ketones: A highly diastereoselective synthetic route to anti-γ-hydroxy-β-amino alcohols

A highly diastereoselective synthesis of anti-γ-hydroxy β-amino alcohols via Zn(BH4)2 reductions of serine derived α-amino ketones is described. The latter were prepared from a serine derived γ-amino-β-ketosulfone via a α-alkylation-

α-Amino Acids as Chiral Educts for Asymmetric Products. Amino Acylation with N-Acylamino Acids

α-N-Acylamino acids have been developed as useful reagents for the preparation of optically pure α-aminoalkylaryl ketones.Protection of the amino group as either the ethoxycarbonyl or benzenesulfonyl derivative allows alanine to serve as an effective educt for the chirally specific synthesis of a variety of structures containing the phenylethylamine backbone.Benzene undergoes Friedel-Crafts acylation with the N-acylalanine acid chloride.Catalyst complexation with oxagenated aromatics, however, prohibits acylation of aryl ethers.An arylmetallo reaction scheme overcomes this problem and also affords regiospecificity not attainable in conventional acylations.As examples, optically pure ephedrines and amphetamines were directly synthesized without recourse to resolution since the chirality of the amino acid educt was entirely conserved throughout the process.