Preparation of N-substituted...

Details Preparation of N-substituted... Preparation of N-substituted...

2006-11-07

2006-11-07

Price, Elvis O. (Department: 1621)

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

Organic compounds

Amino nitrogen containing

Reexamination Certificate

active

07132569

ABSTRACT:
From compounds of formula IIwherein R1and R2are independently of one another H, C1–C6alkyl, C1–C6halogenalkyl, C1–C6alkoxy, C1–C6alkoxy-C1–C6alkyl, or C1–C6alkoxy-C1–C6alkyloxy, R3is C1–C6alkyl, R4is C1–C6alkyl, and R5is 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, R6is C1–C6alkyl, R7is C1–C6alkyl or C1–C6alkoxy, or R6and R7together 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 Iwherein R5is 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 Iais obtained in a high degree of purity.

REFERENCES:
patent: 0 678 503 (1995-10-01), None
Herold, P., et al. “A Versatile and Stereocontrolled Synthesis of Hydroxyethylene Dipeptide Isosters”, Journal of Organic Chemistry, vol. 54, No. 5 (Mar. 1989), pp. 1178-1185.
Cahiez, G., et al. “Highly Stereo- and Chemoselective Iron-Catalyzed Alkenylation of Organomagnesium Compounds”, Synthesis, No. 8 (Aug. 1998), pp. 1199-1200.

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