scholarly journals A NEW SYNTHESIS OF DL-γ-HYDROXY-ORNITHINE

1956 ◽  
Vol 34 (7) ◽  
pp. 911-914 ◽  
Author(s):  
Guy Talbot ◽  
Roger Gaudry ◽  
Louis Berlinguet
Keyword(s):  
Acid Hydrolysis ◽  
Allyl Chloride ◽  
Quantitative Yield ◽  
Dimethyl Formamide ◽  
New Synthesis ◽  
Convenient Synthesis

A convenient synthesis of DL-hydroxy-ornithine is described. Starting from diethyl allylmalonate, it involves treatment with sulphuryl chloride followed by hydrolysis and distillation to give a 90% yield of 2,5-dichloro-4-valerolactone. Condensation of this with two equivalents of potassium phthalimide in dimethyl-formamide gives a quantitative yield of crude 2,5-diphthalimido-4-valerolactone. This lactone is converted quantitatively by acid hydrolysis to DL-γ-hydroxyornithine, isolated as the dihydrochloride of the corresponding 2,5-diamino-4-valerolactone. The over-all yield calculated from allyl chloride is 80%.

A CONVENIENT SYNTHESIS OF DL-GLUTAMIC ACID FROM β-PROPIOLACTONE

1956 ◽  
Vol 34 (10) ◽  
pp. 1440-1443 ◽  
Author(s):  
Guy Talbot ◽  
Roger Gaudry ◽  
Louis Berlinguet
Keyword(s):  
Glutamic Acid ◽  
Acid Hydrolysis ◽  
Sodium Salt ◽  
Intermediate Product ◽  
Diethyl Ester ◽  
New Synthesis ◽  
Convenient Synthesis

A new synthesis of DL-glutamic acid was carried out in an over-all yield of 87% from condensation between β-propiolactone and the sodium salt of diethyl acetamidomalonate, followed by acid hydrolysis. When desired, the intermediate product, the diethyl ester of N-acetyl-2-carbethoxyglutamic acid, could be isolated in a 68% yield and hydrolyzed to glutamic acid via the hydrochloride in a 95% yield.

The synthesis of Cyclododecane-r-1,c-5,c-9-triamine and r-1,c-5,c-9-Tris(2,3-dimethoxybenzamido)cyclododecane

1975 ◽  
Vol 28 (3) ◽  
pp. 673 ◽  
Author(s):  
DJ Collins ◽  
C Lewis ◽  
JM Swan
Keyword(s):  
Aqueous Solution ◽  
Acid Hydrolysis ◽  
Sulphuric Acid ◽  
Sodium Carbonate ◽  
Sodium Azide ◽  
Room Temperature ◽  
Dimethyl Formamide ◽  
Lithium Aluminium Hydride ◽  
Lithium Aluminium ◽  
Hydrolysis Of

Treatment of cyclododecane-r-1,c-5,c-9-triyl tris(p-toluenesulphonate) with sodium azide in dimethyl-formamide at 100� for 6 h gave the corresponding cis,cis-triazide which upon hydrogenation or reduction with lithium aluminium hydride gave cyclododecane-r-1,c-5,c-9-triamine, isolated as the tris-salicylidene derivative. Acid hydrolysis of this, removal of the salicylaldehyde, and treatment of the aqueous solution with sodium carbonate and 2,3-dimethoxybenzoyl chloride gave r-1,c-5,c- 9-tris(2,3-dimethoxybenzamido)cyclododecane. ��� Treatment of (E,E,E)-cyclododeca-1,5,9-triene with an excess of acetonitrile and sulphuric acid at room temperature for three days gave 18% of (E,E)-1-acetamidocyclododeca-4,8-diene; no di- or tri-amides were isolated.

Bequeme Synthese von cis-1,2- Bis(diphenylphosphino)ethanplatin(II)- acetyliden / Convenient Synthesis of cis-1,2-Bis(diphen3dphosphino)- ethane-platinum (II) -acetylides

1983 ◽  
Vol 38 (9) ◽  
pp. 1156-1158 ◽  
Author(s):  
Angelika Sebald ◽  
Bernd Wrackmeyer
Keyword(s):  
Quantitative Yield ◽  
Multinuclear Nmr ◽  
Convenient Synthesis

Abstract The title compounds (1) are obtained in quantitative yield from the reaction between dppePtCl2 (2) and alkynyl stannanes (CH3)3 Sn - C ≡ C-R (3) or (CH3)2Sn(C ≡ C-R)2 (4) in boiling tetrahydrofurane. The complexes 1 have been characterised by multinuclear NMR (13PC, 31P, 195Pt).

Thermal rearrangement of functionalized 1,2-divinylcyclopropane systems. A convenient synthesis of substituted 4-cyclohepten-1-ones

1986 ◽  
Vol 64 (1) ◽  
pp. 180-187 ◽  
Author(s):  
Edward Piers ◽  
Max S. Burmeister ◽  
Hans-Ulrich Reissig
Keyword(s):  
Acid Hydrolysis ◽  
The Other ◽  
Thermal Rearrangement ◽  
Enol Ethers ◽  
Acyl Chlorides ◽  
Silyl Ethers ◽  
Convenient Synthesis ◽  
Enol Silyl Ethers ◽  
Hydrolysis Of ◽  
Subsequent Acid

Reaction of the acyl chlorides 14–21 with lithium (phenylthio)(cis-2-vinylcyclopropyl)cuprate (2) provided the ketones 22–29. Compounds 22–25, upon treatment with i-Pr2NLi-Me3SiCl, were converted cleanly into the enol silyl ethers 30–33, which gave the 1,4-cycloheptadienes 34–37 upon thermolysis (100–110 °C). Acid hydrolysis of the latter materials produced the corresponding 4-cyclohepten-1-ones 38–41. However, subjection of the cis-2-vinylcyclopropyl ketones 26–29 to i-Pr2NLi-t-BuMe2SiCl afforded, in each case, a mixture of isomeric enol ethers (26 → 42 + 44 (1:1); 27 → 43 + 45 (1:9); 28 → 56 + 58 (1:1); 29 → 57 + 59 (4:1)). Thermolysis (150–175 °C) of these mixtures, followed by acid hydrolysis of the resultant products, gave the 4-cyclohepten-1-ones 54, 55, 64, and 65, admixed with the corresponding 3-methylenecyclopentenes 52, 53, 62, and 63. On the other hand, treatment of the trans-2-vinylcyclopropyl ketones 70–74 with i-Pr2NLi–t-BuMe2SiCl provided exclusively or predominantly the enol ethers 75–79. Thermolysis (230 °C) of the latter materials and subsequent acid hydrolysis of the resultant products 80, 50, 51, 60, and 61 afforded the 4-cyclopenten-1-ones 38, 54, 55, 64, and 65.

THE SYNTHESIS OF D,L-α-AMINO-ε-HYDROXYCAPROIC ACID AND A NEW SYNTHESIS OF D,L-LYSINE

1948 ◽  
Vol 26b (4) ◽  
pp. 387-392 ◽  
Author(s):  
Roger Gaudry
Keyword(s):  
Amino Acids ◽  
Acid Hydrolysis ◽  
Hydrobromic Acid ◽  
Starting Material ◽  
New Synthesis ◽  
Strecker Synthesis ◽  
Hydrolysis Of ◽  
Bromo Compound

δ-Hydroxyvaleraldehyde, obtained by acid hydrolysis of dihydropyran, is a convenient starting material for the synthesis of D,L-lysine. Application to the aldehyde of the Bucherer modification of the Strecker synthesis for α-amino acids yields 5-δ-hydroxybutylhydantoin which is hydrolyzed into D,L-α-amino-ε-hydroxycaproic acid. D,L-Lysine is obtained from 5-δ-hydroxybutylhydantoin by bromination with hydrobromic acid into 5-δ-bromobutylhydantoin, amination of the bromo compound with ammonia, and hydrolysis of the hydantoin ring into D,L-lysine, readily isolated as the dipicrate.

A new synthesis of 2,10,11-trioxatricyclo[4.4.4.01,6]tetradecane

1980 ◽  
Vol 58 (9) ◽  
pp. 875-877 ◽  
Author(s):  
Normand Beaulieu ◽  
Pierre Deslongchamps
Keyword(s):  
New Synthesis ◽  
Convenient Synthesis

A simple and convenient synthesis of tricyclic orthoester 1 (2,10,11-trioxatricyclo[4.4.4.01,6]tetradecane) is described.

A new synthesis of tetra(quinoxalino)tetraazaporphyrin by the retro Diels-Alder reaction of a soluble precursor

2006 ◽  
Vol 10 (10) ◽  
pp. 1197-1201 ◽  
Author(s):  
Tetsuo Okujima ◽  
Makoto Kikuchi ◽  
Hiroko Yamada ◽  
Hidemitsu Uno ◽  
Noboru Ono
Keyword(s):  
Alder Reaction ◽  
Diels Alder ◽  
Quantitative Yield ◽  
Diels Alder Reaction ◽  
New Synthesis

Soluble tetra(pyrazino)tetraazaporphyrin was synthesized by the reaction of bicyclo[2.2.2]octadiene-fused dicyanopyrazine. The retro Diels-Alder reaction of the soluble tetra(pyrazino)tetraazaporphyrin gave a tetra(quinoxalino)tetraazaporphyrin in quantitative yield.

A New Synthesis of Pyrazino[2,3-c]isoquinolines

1990 ◽  
Vol 43 (1) ◽  
pp. 179 ◽  
Author(s):  
MRM Bates ◽  
LW Deady ◽  
MF Mackay
Keyword(s):  
Crystal Structure ◽  
Ethyl Pyruvate ◽  
Ring Closure ◽  
Full Matrix ◽  
Space Group ◽  
Nucleophilic Displacement ◽  
New Synthesis ◽  
Convenient Synthesis ◽  
Displacement Reactions ◽  
Title System

A convenient synthesis of 1-(p-chlorophenoxy )isoquinoline-3,4-diame is described. Condensation with ethyl pyruvate gave entry to the tricyclic title system, and some further nucleophilic displacement reactions of substituent groups are described. The direction of ring closure in the tricycle formation was proved by determining the crystal structure of one of the derivatives; rhombohedral crystals of (3b) belong to the space group R3 with a 21.822(5)Ǻ, α 116.81(2)° and Z 12. Full-matrix refinement using 3093 reflections converged at R 0.085.

A convenient synthesis of homochiral δ-alkylated α,β-unsaturated δ-lactones

1991 ◽  
Vol 56 (5) ◽  
pp. 1042-1051 ◽  
Author(s):  
Thomas Høyer ◽  
Anders Kjær ◽  
Jens Lykkesfeldt
Keyword(s):  
Acid Hydrolysis ◽  
Boron Trifluoride ◽  
Tert Butyl ◽  
Convenient Synthesis

The tert-butyl propiolate ion serves as a convenient and efficient nucleophile in boron trifluoride-catalyzed openings of homochiral, mono-substituted epoxides. The resulting tert-butyl 5-hydroxy-2-alkynoates are converted into the title compounds upon semihydrogenation followed by acid hydrolysis. Specific examples include the synthesis of parasorbic acid and massoilactone, two naturally derived lactones of the present type. The scope of the synthetic protocol is discussed.

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