Process for the preparation of phosphorus-containing L-amino acids, their derivatives and intermediates for this process
First Claim
1. A process for the preparation of a compound of the formula I or salt thereof, ##STR16## in which R1 and R2 independently of each other are hydrogen, (C1 -C6)-alkyl, which is unsubstituted or is mono- of polysubstituted by halogen or aryl, or (C3 -C10)-cycloalkyl,R3 and R4 independently of each other are hydrogen, (C1 -C6)-alkyl, (C2 -C6)-alkenyl, (C2 -C6)-alkynyl, where the last three radicals mentioned can be straight-chain or branched and can have hetero atoms in the chain, (C1 -C6)-alkylcarbonyl, aryl-(C1 -C4)-alkylcarbonyl, (C1 -C6)-alkoxycarbonyl, (C1 -C6)-alkylsulfonyl, benzyl, benzyloxycarbonyl, aryloxycarbonyl or arylsulfonyl, where the last four radicals mentioned are unsubstituted or substituted in the aryl radical,R5 is hydrogen or (C1 -C4)-alkyl, which is straight-chain or branched and is unsubstituted or substituted by halogen, aryl or a heterocycle, or (C3 -C7)-cycloalkyl andn is the number 0 or 1,which comprisesa) reacting an optically active S-homoserine lactone of the formula II, ##STR17## in which R3 and R4 are defined as in formula I, with hydrogen chloride in the presence of an alcohol of the formula R5 --OH to give a compound of the formula III ##STR18## in which R3, R4 and R5 are defined as in formula I, except that R5 =H, andb) reacting the resulting compound of formula III with a compound of formula IV,
in whichR1, R2 and n are defined as in formula I and, if desired, hydrolyzing the product to give the compound of formula I, in which R5 =H.
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Abstract
Process for the preparation of phosphorus-containing L-amino acids, their derivatives and intermediates for this process
L-amino acids of the formula I and salts thereof, ##STR1## in which R1 to R5 are defined as in claim 1 and n is 0 or 1, are obtained according to the invention by
a) reacting an optically active S-homoserine lactone of the formula II, ##STR2## with hydrogen chloride in the presence of an alcohol of the formula R5 --OH to give novel compounds of the formula III, ##STR3## in which R3, R4 and R5 are defined as in formula I, except that R5 =H, and
b) reacting the resulting compound of formula III with a compound of formula IV,
R.sup.1 (O).sub.n -R(OR.sup.2).sub.2 (IV)
and if desired, hydrolyzing the product to give a compound of formula I, in which R5 =H.
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Citations
17 Claims
- 1. A process for the preparation of a compound of the formula I or salt thereof, ##STR16## in which R1 and R2 independently of each other are hydrogen, (C1 -C6)-alkyl, which is unsubstituted or is mono- of polysubstituted by halogen or aryl, or (C3 -C10)-cycloalkyl,
R3 and R4 independently of each other are hydrogen, (C1 -C6)-alkyl, (C2 -C6)-alkenyl, (C2 -C6)-alkynyl, where the last three radicals mentioned can be straight-chain or branched and can have hetero atoms in the chain, (C1 -C6)-alkylcarbonyl, aryl-(C1 -C4)-alkylcarbonyl, (C1 -C6)-alkoxycarbonyl, (C1 -C6)-alkylsulfonyl, benzyl, benzyloxycarbonyl, aryloxycarbonyl or arylsulfonyl, where the last four radicals mentioned are unsubstituted or substituted in the aryl radical, R5 is hydrogen or (C1 -C4)-alkyl, which is straight-chain or branched and is unsubstituted or substituted by halogen, aryl or a heterocycle, or (C3 -C7)-cycloalkyl and n is the number 0 or 1, which comprises a) reacting an optically active S-homoserine lactone of the formula II, ##STR17## in which R3 and R4 are defined as in formula I, with hydrogen chloride in the presence of an alcohol of the formula R5 --OH to give a compound of the formula III ##STR18## in which R3, R4 and R5 are defined as in formula I, except that R5 =H, and b) reacting the resulting compound of formula III with a compound of formula IV, - space="preserve" listing-type="equation">R.sup.1 (O).sub.n -P(OR.sup.2).sub.2 (IV)
in which R1, R2 and n are defined as in formula I and, if desired, hydrolyzing the product to give the compound of formula I, in which R5 =H. - View Dependent Claims (2, 3, 4, 5, 6, 11, 12, 13, 14, 15)
- 12. The process as claimed in claim 11, wherein the reaction is carried out at 50°
- to 150°
C.
- 13. The process as claimed in claim 12, wherein the reaction is carried out in the absence of solvent.
- 14. The process as claimed in claim 13, wherein the reaction is carried out at 110°
- to 140°
C.
- 15. The process as claimed in claim 11,
wherein the compound obtained of the formula I is hydrolyzed with 3N to 12N aqueous hydrochloric acid at 90° - to 130°
C. to give the compound of the formula I, in which R5 =H.
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7. A process for the preparation of a compound of formula III ##STR19## which comprises reacting a compound of formula II ##STR20## with hydrogen chloride in the presence of an alcohol of the formula R5 --OH, and, if desired, hydrolyzing the product to give the compound of formula III in which R5 =H wherein:
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R3 and R4 independently of each other are hydrogen, (C1 -C6)-alkyl, (C2 -C6)-alkenyl, (C2 -C6)-alkynyl, where the last three radicals mentioned can be straight-chain or branched and can have hetero atoms in the chain, (C1 -C6)-alkylcarbonyl, aryl-(C1 --C4)-alkylcarbonyl, (C1 -C6)-alkoxycarbonyl, (C1 -C6)-alkylsulfonyl, benzyl, benzyloxycarbonyl, aryloxycarbonyl or arylsulfonyl, where the last four radicals mentioned are unsubstituted or substituted in the aryl radical, and R5 is hydrogen or (C1 -C4)-alkyl, which is straight-chain or branched and is unsubstituted or substituted by halogen, aryl or a heterocycle, or (C3 -C7)-cycloalkyl. - View Dependent Claims (8, 9, 10)
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16. A compound of the formula III or a salt thereof ##STR22## wherein:
- R3 is H, R4 is p-tosyl, and R5 is ethyl.
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17. A compound of the formula III or a salt thereof ##STR23## wherein:
- R3 is H, R4 is methoxycarbonyl, and R5 is ethyl.
Specification
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- Resources
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Current AssigneeHoechst Schering AgrEvo GmbH (Bayer AG)
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Original AssigneeHoechst Aktiengesellschaft (Sanofi )
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InventorsHoffmann, Michael
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Primary Examiner(s)Lee, Mary C.
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Assistant Examiner(s)AMBROSE, MICHAEL GEORGE
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Application NumberUS08/271,775Time in Patent Office404 DaysField of Search558/124, 560/150, 560/161, 560/172, 560/12, 562/574US Class Current560/12CPC Class CodesC07C 229/20 the carbon skeleton being f...C07C 271/22 to carbon atoms of hydrocar...C07C 311/06 to acyclic carbon atoms of ...C07C 311/19 to an acyclic carbon atom o...C07F 9/301 Acyclic saturated acids whi...C07F 9/3211 Esters of acyclic saturated...C07F 9/3808 Acyclic saturated acids whi...
