Preparation of N-substituted 2,7-dialkyl-4-hydroxy-5-amino-8-aryl-octanoyl amides
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United States of America Patent
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Nov 7, 2006
Issued Date -
N/A
app pub date -
Oct 21, 2005
filing date -
Jul 29, 1999
priority date (Note) -
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status (Latency Note)
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Abstract
From compounds of formula II ##STR00001## wherein R.sub.1 and R.sub.2 are independently of one another H, C.sub.1 C.sub.6alkyl, C.sub.1 C.sub.6halogenalkyl, C.sub.1 C.sub.6alkoxy, C.sub.1 C.sub.6alkoxy-C.sub.1 C.sub.6alkyl, or C.sub.1 C.sub.6alkoxy-C.sub.1 C.sub.6alkyloxy, R.sub.3 is C.sub.1 C.sub.6alkyl, R.sub.4 is C.sub.1 C.sub.6alkyl, and R.sub.5 is C.sub.1 C.sub.6alkyl, C.sub.1 C.sub.6hydroxyalkyl, C.sub.1 C.sub.6alkoxy-C.sub.1 C.sub.6-alkyl, C.sub.1 C.sub.6alkanoyloxy-C.sub.1 C.sub.6alkyl, C.sub.1 C.sub.6aminoalkyl, C.sub.1 C.sub.6alkylamino-C.sub.1 C.sub.6-alkyl, C.sub.1 C.sub.6-dialkylamino-C.sub.1 C.sub.6-alkyl, C.sub.1 C.sub.6-alkanoylamido-C.sub.1 C.sub.6-alkyl, HO(O)C--C.sub.1 C.sub.6-alkyl, C.sub.1 C.sub.6alkyl-O--(O)C--C.sub.1 C.sub.6alkyl, H.sub.2N--C(O)--C.sub.1 C.sub.6alkyl, C.sub.1 C.sub.6alkyl-HN--C(O)--C.sub.1 C.sub.6alkyl or (C.sub.1 C.sub.6alkyl).sub.2N--C(O)--C.sub.1 C.sub.6-alkyl, R.sub.6 is C.sub.1 C.sub.6alkyl, R.sub.7 is C.sub.1 C.sub.6alkyl or C.sub.1 C.sub.6alkoxy, or R.sub.6 and R.sub.7 together are tetramethylene, pentamethylene, 3-oxa-1,5-pentylene or --CH.sub.2CH.sub.2O-- substituted, if necessary, with C.sub.1 C.sub.4-Alkyl, phenyl or benzyl, it is possible--through halolactonization, azidation of the halogen group, ring opening with an amine R.sub.5--NH.sub.2, and reduction of the azide group to form the amino group--to prepare compounds of formula I ##STR00002## wherein R.sub.5 is C.sub.1 C.sub.6alkyl, C.sub.1 C.sub.6hydroxyalkyl, C.sub.1 C.sub.6alkoxy-C.sub.1 C.sub.6alkyl, C.sub.1 C.sub.6alkanoyloxy-C.sub.1 C.sub.6alkyl, C.sub.1 C.sub.6aminoalkyl, C.sub.1 C.sub.6alkylamino-C.sub.1 C.sub.6alkyl, C.sub.1 C.sub.6dialkylamino-C.sub.1 C.sub.6-alkyl, C.sub.1 C.sub.6alkanoylamido-C.sub.1 C.sub.6alkyl, HO(O)C--C.sub.1 C.sub.6alkyl, C.sub.1 C.sub.6alkyl-O--(O)C--C.sub.1 C.sub.6alkyl, H.sub.2N--C(O)--C.sub.1 C.sub.6alkyl, C.sub.1 C.sub.6alkyl-HN--C(O)--C.sub.1 C.sub.6alkyl or (C.sub.1 C.sub.6alkyl).sub.2--N--C(O)--C.sub.1 C.sub.6alkyl. If 2(S),7(R)-diastereomer of formula II is used, the 2(S),4(S),5(S),7(S)-diastereomer of formula Ia ##STR00003## is obtained in a high degree of purity.
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