Hydroxyproline derivatives and preparative process therefor

Details Hydroxyproline derivatives and preparative process therefor Hydroxyproline derivatives and preparative process therefor

1994-05-04

1995-01-10

Brust, Joseph P.

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

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

546174, 546208, 546281, 548260, 548519, C07D20712

Patent

active

053808754

ABSTRACT:
Provided are N-(9-fluorenylmethoxycarbonyl)-4-substituted proline derivatives represented by the following formula (I): ##STR1## wherein Q is O or S, R represents a particular monovalent group, and T represents H or --C(CH.sub.3).sub.3. Where T is H, the derivatives can each be prepared by reacting a corresponding electron attractive compound with N-(9-fluorenylmethoxycarbonyl)-4-hydroxyproline in the presence of a coupling reagent. The derivatives in which T stands for --(CH.sub.3).sub.3 can each be prepared by reacting the corresponding N-(9-fluorenylmethoxy-carbonyl)-4-hydroxyproline derivative with isobutylene in the presence of a catalytic amount of sulfuric acid. The staring material, N-(9-fluorenylmethoxycarbonyl)-4-hydroxyproline, can be purified by adsorbing it on anhydrous magnesium sulfate.

REFERENCES:
patent: 5101059 (1992-03-01), Carpino et al.
Carpino, et al.; J. Org. Chem., (1972), pp. 3404-3409.
Meienhofer, et al.; Peptide Protein Research, (1979), pp. 35-42.
Schon, et al.; Synthesis-Communications, (1986), pp. 303-305.
LaPatsanis, et al.; Synthesis-Communications, (1983), pp. 671-673.
Kisfaludy, et al., Synthesis-Communications (1983), pp. 325-327.

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