Method of producing oxazolidinones, the use thereof and novel ox

Details Method of producing oxazolidinones, the use thereof and novel ox Method of producing oxazolidinones, the use thereof and novel ox

1997-08-21

2000-04-18

Raymond, Richard L.

Organic compounds -- part of the class 532-570 series

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

C07D26304

Patent

active

060517158

DESCRIPTION:

BRIEF SUMMARY
The invention is relative to methods of producing oxazolidinones of general formula I ##STR1## in which R.sup.1 signifies hydrogen; (C.sub.1 -C.sub.12)-alkyl; (C.sub.2 -C.sub.10)-alkenyl; (C.sub.2 -C.sub.10)-alkenyl; (C.sub.1 -C.sub.6)-alkyl which is substituted singly or multiply by equal or different groups from the group of halogen, (C.sub.1 -C.sub.4)-alkoxy, (C.sub.1 -C.sub.4)-alkylthio, --CN, (C.sub.2 -C.sub.5)-alkoxycarbonyl and (C.sub.2 -C.sub.6)-alkenyl; (C.sub.3 -C.sub.8)-cycloalkyl which is unsubstituted or substituted by one or more groups from the group (C.sub.1 -C.sub.4)-alkyl, (C.sub.1 -C.sub.4)-alkoxy, (C.sub.1 -C.sub.4)-alkylthio and halogen; (C.sub.5 -C.sub.8)-cycloalkenyl; aryl or aryl-(C.sub.1 -C.sub.4)-alkyl which are unsubstituted or substituted in the aryl group; --OR.sup.6 ; NR.sup.7 R.sup.8 ; or stands in conjunction with the adjacent carbonyl group for a protective group, especially boac, Z, TFA, aloc, teoc, formyl, tosyl, mesyl, fmoc, moc, suitable for protecting the amino group of an amino acid; differently hydrogen, (C.sub.1 -C.sub.8)-alkyl or (C.sub.3 -C.sub.8)-alkenyl, (C.sub.3 -C.sub.8)-alkenyl or (C.sub.3 -C.sub.8)-cycloalkyl, or multiply, preferably up to three times, by equal or different groups from the group containing halogen, hydroxy, (C.sub.1 -C.sub.8)-alkoxy, (C.sub.1 -C.sub.8)-alkylmercapto, (C.sub.2 -C.sub.8)-alkenylmercapto, (C.sub.2 -C.sub.8)-alkinylmercapo, (C.sub.2 -C.sub.8)-alkenyloxy, (C.sub.2 -C.sub.8)-alkinyloxy, (C.sub.3 -C.sub.7)-cycloalkyl, (C.sub.3 -C.sub.7)-cycloalkoxy, cyano, mono- and di-(C.sub.1 -C.sub.4 -alkyl)-amino, aryl, aryl-(C.sub.1 -C.sub.6)-alkoxy, which last two groups cited in the aryl ring can be unsubstituted or substituted singly or multiply, preferably up to three times, by equal or different groups from the group of halogen, (C.sub.1 -C.sub.4)-alkyl, (C.sub.1 -C.sub.4)-alkoxy, (C.sub.1 -C.sub.4)-halogen alkyl, (C.sub.1 -C.sub.4)-halogen alkoxy; and ring which can also be N, O, S-heterosubstituted itself in addition to the cited substituents; -C.sub.6)-alkenyl, (C.sub.2 -C.sub.6)-alkinyl, aryl, alkaryl, aryl alkyl or cycloalkyl and the linear as well as the branched alkyl groups can contain halogen- and/or heteroatom substitution (N, O, S) either singly or multiply, just as the aliphatic or aromatic cycles; substituted with up to four (C.sub.1 -C.sub.4)-alkyl groups, (C.sub.3 -C.sub.4)-alkenyl groups, (C.sub.3 -C.sub.4)-alkinyl groups, (C.sub.3 -C.sub.8)-cycloalkyl groups and/or aryl groups, which alkane diyl chain itself as well as its substituents can be N, O, S-heterosubstituted one another or one of the substituents of the alkane diyl chain with R.sup.4 even to a ring; -C.sub.12)-cycloalkyl, (C.sub.2 -C.sub.8)-alkenyl or (C.sub.2 -C.sub.8)-alkinyl, which above C-containing groups are unsubstituted or substituted singly or multiply, preferably up to three times, by equal or different groups from the group containing halogen, hydroxy, (C.sub.1 -C.sub.8)-alkoxy, (C.sub.1 -C.sub.8)-alkylmercapto, (C.sub.2 -C.sub.8)-alkenylmercapto, (C.sub.2 -C.sub.8)-alkinylmercapto, (C.sub.2 -C.sub.8)-alkenyloxy, (C.sub.2 -C.sub.8)-alkinyloxy, (C.sub.3 -C.sub.7)-cycloalkyl, (C.sub.3 -C.sub.7)-cycloalkoxy, cyano, mono- and di-(C.sub.1 -C.sub.4 -alkyl)-amino, carboxy, (C.sub.1 -C.sub.8)-alkoxycarbonyl, -C.sub.4) -alkyl, 1-[(C.sub.1 -C.sub.4)-alkoxyimino]-(C.sub.1 -C.sub.6)-alkyl, amino, by halogen, nitro, (C.sub.1 -C.sub.4)-alkoxy or optionally substituted phenyl, (C.sub.2 -C.sub.6)-alkenylcarbonyloxy, (C.sub.2 -C.sub.6)-alkinylcarbonyloxy, (C.sub.1 -C.sub.8) -alkylsulfonyl, phenyl, phenyl-(C.sub.1 -C.sub.6)-alkoxy, phenyl-(C.sub.1 -C.sub.6) -alkoxycarbonyl, phenoxy, phenoxy-(C.sub.1 -C.sub.6)-alkoxy, phenoxy-(C.sub.1 -C.sub.6) -alkoxycarbonyl, phenylcarbonyloxy, phenylcarbonyl amino, phenyl-(C.sub.1 -C.sub.6)-alkylcarbonyl amino, which last-named 9 groups in the phenyl ring are unsubstituted or substituted simply or multiply, preferably up to three times, by equal or different groups from the group of halogen, (C.sub.1 -C.sub.4) -alkyl, (C.sub.1 -C.sub

REFERENCES:
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Patent Abstract of Japan, vol. 6, No. 231 (C-135), Nov. 17, 1982, & JP,A,57 134452, Aug. 19, 1982, see abstract.
Synthesis, No. 11, Nov. 1991, pp. 935-936, XP002005519, Lee et al: "Regioselective amidation of aspartic and glutamic acid", see the whole document.
Chemical Abstracts, vol. 117, No. 25, Dec. 21, 1992, abstract No. 251789t, Ascher g & Ludescher h.: "Preparation of aspartylphenylalanine alkyl esters from 5-oxo-4-oxazolideneacetates and phenylalanine esters", p. 740; col 1; XP002005520, see abstract & AT,A, 394 854, Jul. 10, 1992.

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