Production of N-substituted 2,7-dialkyl-4-hydroxy-5-amino-8-arly-octanoylamides

Abstract

From compounds of formula II wherein R1 and R2 are independently of one another H, C1–C6alkyl, C1–C6halogenalkyl, C1–C6alkoxy, C1–C6alkoxy-C1–C6alkyl, or C1–C6alkoxy-C1–C6alkyloxy, R3 is C1–C6alkyl, R4 is C1–C6alkyl, and R5 is C1–C6alkyl, C1–C6hydroxyalkyl, C1–C6alkoxy-C1–C6-alkyl, C1–C6alkanoyloxy-C1–C6alkyl, C1–C6aminoalkyl, C1–C6alkylamino-C1–C6-alkyl, C1–C6-dialkylamino-C1–C6-alkyl, C1–C6-alkanoylamido-C1–C6-alkyl, HO(O)C—C1–C6-alkyl, C1–C6alkyl-O—(O)C—C1–C6alkyl, H2N—C(O)—C1–C6alkyl, C1–C6alkyl-HN—C(O)—C1–C6alkyl or (C1–C6alkyl)2N—C(O)—C1–C6-alkyl, R6 is C1–C6alkyl, R7 is C1–C6alkyl or C1–C6alkoxy, or R6 and R7 together are tetramethylene, pentamethylene, 3-oxa-1,5-pentylene or —CH2CH2O— substituted, if necessary, with C1–C4-Alkyl, phenyl or benzyl, it is possible—through halolactonization, azidation of the halogen group, ring opening with an amine R5—NH2, and reduction of the azide group to form the amino group—to prepare compounds of formula I wherein R5 is C1–C6alkyl, C1–C6hydroxyalkyl, C1–C6alkoxy-C1–C6alkyl, C1–C6alkanoyloxy-C1–C6alkyl, C1–C6aminoalkyl, C1–C6alkylamino-C1–C6alkyl, C1–C6dialkylamino-C1–C6-alkyl, C1–C6alkanoylamido-C1–C6alkyl, HO(O)C—C1–C6alkyl, C1–C6alkyl-O—(O)C—C1–C6alkyl, H2N—C(O)—C1–C6alkyl, C1–C6alkyl-HN—C(O)—C1–C6alkyl or (C1–C6alkyl)2—N—C(O)—C1–C6alkyl. If 2(S), 7(R)-diastereomer of formula II is used, the 2(S), 4(S), 5(S), 7(S)-diastereomer of formula Ia is obtained in a high degree of purity.

Dependencies are inferred from the claim text.