Hydrogenation of .beta.-amino-.alpha.,.beta.-unsaturated esters

Augustine, Robert L.; Bellina, Russell F.; Gustavsen, A. J.

doi:10.1021/jo01267a095

Cited by 9 publications

(3 citation statements)

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“…The combined organic layers were dried over MgSO 4 and concentrated under reduced pressure. 4g was isolated as a white solid (0.98 g) and used in the next reaction without further purification; mp 56 °C (lit . mp 58−60.5 °C).…”

Section: Methodsmentioning

confidence: 99%

Chemo-Enzymatic Synthesis of (2S,4R)-2-Amino-4-(3-(2,2-diphenylethylamino)-3-oxopropyl)pentanedioic Acid: A Novel Selective Inhibitor of Human Excitatory Amino Acid Transporter Subtype 2

et al. 2008

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In the mammalian central nervous system (CNS), the action of sodium dependent excitatory amino acid transporters (EAATs) is responsible for termination of glutamatergic neurotransmission by reuptake of ( S) -glutamate (Glu) from the synaptic cleft. Five EAAT subtypes have been identified, of which EAAT1-4 are present in the CNS, while EAAT5 is localized exclusively in the retina. In this study, we have used an enantioselective chemo-enzymatic strategy to synthesize 10 new Glu analogues 2a- k ( 2d is exempt) with different functionalities in the 4 R-position and characterized their pharmacological properties at the human EAAT1-3. In particular, one compound, 2k, displayed a significant preference as inhibitor of the EAAT2 subtype over EAAT1,3. The compound also displayed very low affinities toward ionotropic and metabotropic Glu receptors, making it the most selective EAAT2 inhibitor described so far.

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Section: Methodsmentioning

confidence: 99%

Chemo-Enzymatic Synthesis of (2S,4R)-2-Amino-4-(3-(2,2-diphenylethylamino)-3-oxopropyl)pentanedioic Acid: A Novel Selective Inhibitor of Human Excitatory Amino Acid Transporter Subtype 2

et al. 2008

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“…Further saturation of vinylogous amides such a s 68 requires the use of either a palladium[84] o r rhodium[85] catalyst at 85 t o 100°C and 500 to 1000 psig of hydrogen.…”

mentioning

confidence: 99%

Organic Functional Group Hydrogenation

Augustine

1976

Catalysis Reviews

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“…To improve the cost efficiency and scalability of the process, we turned our attention toward catalytic reduction of the enamine . It was difficult to achieve complete conversion with Pd/C despite high H 2 pressure (350 psi) and high catalyst loading (10% to 20%).…”

Section: Resultsmentioning

confidence: 99%

Scalable Non-Aqueous Process to Prepare Water Soluble 3-Amino-pentan-1,5-diol

Rawalpally

Cleary

et al. 2009

Org. Process Res. Dev.

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The development of a nonaqueous process for the synthesis of 3-amino-pentan-1,5-diol is described. Beginning with dimethyl acetone-1,3-dicarboxylate, a telescoped sequence of reductive amination, Boc protection, sodium borohydride reduction, and acidic resin-mediated deprotection generates the title compound. The key to this efficient process is the telescoped deprotection, purification and nonaqueous isolation of the 3-amino-pentan-1,5diol. The process involves four optimized chemical reactions using two solvents in 89% overall yield and 97-98 area % purity.

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Hydrogenation of .beta.-amino-.alpha.,.beta.-unsaturated esters

Cited by 9 publications

References 0 publications

Chemo-Enzymatic Synthesis of (2S,4R)-2-Amino-4-(3-(2,2-diphenylethylamino)-3-oxopropyl)pentanedioic Acid: A Novel Selective Inhibitor of Human Excitatory Amino Acid Transporter Subtype 2

Chemo-Enzymatic Synthesis of (2S,4R)-2-Amino-4-(3-(2,2-diphenylethylamino)-3-oxopropyl)pentanedioic Acid: A Novel Selective Inhibitor of Human Excitatory Amino Acid Transporter Subtype 2

Organic Functional Group Hydrogenation

Scalable Non-Aqueous Process to Prepare Water Soluble 3-Amino-pentan-1,5-diol

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