- Α-substd. provitamin optically active production of phosphorus
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PROBLEM TO BE SOLVED: To provide an industrial method practically suitable for producing an optically active α-substituted prolines with short process and mild conditions.SOLUTION: A method of producing an optically active α-substituted prolines (6) includes (d) a step of obtaining an optically active N, α-substituted prolines (5) by hydrolysis of an optically active N, α-substituted proline amides (4), and (e) a step of obtaining an optically active α-substituted prolines (6) by eliminating the optically active N, and a protective group Rof the α-substituted prolines (5).
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- METHOD FOR PRODUCING OPTICALLY ACTIVE ALPHA-SUBSTITUTED PROLINE
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The present invention aims to provide an industrial method practically suitable for producing optically active α-substituted prolines from an acyclic ketone compound by a small number of steps under mild conditions. The present invention relates to a production method of an optically active α-substituted proline (4) and/or an optically active α-substituted prolinamide (5), including (a) reacting an acyclic ketone compound (1) with at least one selected from ammonia, an ammonium salt, primary amine and a salt of primary amine, and a cyanating agent to give a cyclic nitrogen-containing compound (2), (b) hydrating the cyclic nitrogen-containing compound (2) to give an α-substituted prolinamide (3), and (c) resolving the α-substituted prolinamide (3) by one or more of (d) enzymatical hydrolysis, (e) resolution by diastereomeric salt formation, and (f) separation by column chromatography.
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- 2-Carboxamide Cycloamino Ureas
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The present invention relates to compounds of formula I and salts thereof, wherein the substituents are as defined in the description, to compositions and use of the compounds in the treatment of diseases ameloriated by inhibition of phosphatidylinositol
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Page/Page column 18
(2011/01/12)
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- Is the backbone conformation of Cα-methyl proline restricted to a single region?
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Cα-Methyl-L-proline, or L(αMe)Pro, is probably the most conformational constrained α-amino acid. In particular, its ω and o torsion angles are restricted to about 180 and -60°, respectively, and only three ranges of values are theoretically ava
- De Poli, Matteo,Moretto, Alessandro,Crisma, Marco,Peggion, Cristina,Formaggio, Fernando,Kaptein, Bernard,Broxterman, Quirinus B.,Toniolo, Claudio
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experimental part
p. 8015 - 8025
(2010/03/31)
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- Organic Compounds
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The present invention relates to compounds of formula I and its salts, wherein the substituents are as defined in the description, to compositions and use of the compounds in the treatment of diseases ameloriated by inhibition of phosphatidylinositol 3-kinase.
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Page/Page column 38
(2009/07/10)
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- ORGANIC COMPOUNDS
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The resent invention relates to a com ound of formula (I) and its salts, wherein the substituents are as defined in the description, to compositions and use of the compounds in the treatment of diseases ameloriated by inhibition of phosphatidylinositol 3-
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Page/Page column 43
(2009/07/25)
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- Preparation and Use of Chloromethyl (-)-Menthyl Ether in the Synthesis of Optically Pure α-Branched α-Amino Nitriles
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The synthesis of optically pure chloromethyl (-)-menthyl ether (2b) and its use in the synthesis of di-(-)-menthyl acetal (-)-menthyl (+)-menthyl acetals are described.The diastereomeric mixed acetals 7a,b and 8a,b are easily obtainable from the nitrones 5 and 6, KCN and 2b.The mixture of diastereomers are separated into the pure components 7a, 7b and 8a, 8b by simple silica gel column chromatography.Hydrolysis of these products (H2O2/Na2CO3, ultrasound) followed by N-O cleavage affords the heterocyclic α-methyl-α-amino amides 11a, 11b and 12a, 12b.These are subsequently hydrolyzed to give the corresponding α-methyl-α-amino acids with S and R configuration, respectively.
- Shatzmiller, Shimon,Dolithzky, Ben-Zion,Bahar, Eliezer
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p. 375 - 379
(2007/10/02)
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