Amino protecting group

Details Amino protecting group Amino protecting group

1991-08-19

1992-12-08

Berch, Mark L.

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

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

540222, 540226, 540227, 540228, 540229, 540230, 540301, 540360, 540363, 540364, C07B 5700, C07D205085, C07D46300, C07D205095

Patent

active

051699451

ABSTRACT:
The present invention provides a process for protecting an amino group in a compound exposed to nucleophilic reaction conditions in which the imido group used for protection is reacted with a secondary amine to form an acyl group which protects the amino group during exposure to the nucleophilic reaction conditions, after which the acylamino group may be reacted with an acid to reform the imido group so that the compound may then undergo non-nucleophilic manipulations. Also provided is a resolution method in which diasteriometric compounds having the acylamino group as described above are reacted with acid, and as these diasteriomers react at different rates to form the imido group, the reaction may be monitored so as to isolate the desired product at the appropriate point to maximize optical purity.

REFERENCES:
patent: 3905966 (1975-09-01), Kukolja et al.
patent: 4085100 (1978-04-01), Kingsbury
Kato, Chem. Abs. 70, 114787n (1968).
Ganin, J. Org. Chem. U.S.S.R. 21, 2205 (1985).
Pastor, J. Org. Chem. 53, 5776 (1988).
Wolfe, S. and Hasen, S. K., Canadian Journal of Chemistry, 48, 3572 (1970).
Osby et al., Tetrahedron Letters, vol. 25, No. 20, pp. 2093-2096, 1984.
Gibson, M. S., and Bradshaw, R. W., "The Gabriel Synthesis of Primary Amines", Angew. Chem. Intemat. Edit., vol. 7 (1968), No. 12, pp. 919-930.
Kukolja, S., and Lammert, S. R., J.A.C.S., 97: A, Sep. 17, 1975.
Kukolja et al., Croatica Chemica Acta, 49, (4), pp. 779-795 (1977).
Kume et al., Tetrahedron Letters, vol. 23, No. 42, pp. 4365-4368 (1982).
Logusch, E. W., Tetrahedron Letters, vol. 27, No. 49, pp. 5935-5938 (1986).
Greene, T. W., Protective Groups in Organic Synthesis, New York, John Wiley & Sons, pp. 265-266, (1981).
Uhle, F. C., J. Org. Chem., 26, 2998-3000 (1960).

Affiliated with

Also associated with

Rating

Amino protecting group does not yet have a rating. At this time, there are no reviews or comments for this patent.

If you have personal experience with Amino protecting group, we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Amino protecting group will most certainly appreciate the feedback.

Rate now

Comments { 0 }

Profile ID: LFUS-PAI-O-961807