Process for blocking amino acids with the tertiary-alkoxycarbony

Details Process for blocking amino acids with the tertiary-alkoxycarbony Process for blocking amino acids with the tertiary-alkoxycarbony

1986-03-07

1989-06-06

Schwartz, Richard A.

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

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

548344, 548497, 548533, 562443, 562445, 562446, 562556, 562557, 562560, 562561, 562567, 562571, 562575, C07D23384

Patent

active

048373320

ABSTRACT:
Amino acid salt having at least one unblocked amino group and comprising at least one cation which has a nitrogen cationic atom is reacted with 1-(tertiary-alkoxycarbonyl)imidazole in the liquid phase and in the presence of essentially inert organic solvent having a dielectric constant at 25.degree. C. of at least about 4, to produce N-(tertiary-alkoxycarbonyl)-blocked amino acid salt.

REFERENCES:
Wertheim, E., Textbook of Organic Chemistry, 3rd ed., McGraw Hill, New York, 1951, pp. 280-282, 795 and 796.
Webster's Seventh New Collegiate Dictionary, G and C Merriam Co., Springfield, MA, 1965, p. 669.
U. Ragnarsson et al., Acta Chemica Scandinavica, vol. 26, No. 6, pp. 2550-2551 (1972).
M. Fridkin et al., Canadian Journal of Chemistry, vol. 49, pp. 1578-1581 (1971).
Klee and Brenner, "t-Butylcarbonyl--imidazol und t-Butyloxycarbonyl-hydrazin", Helvetica Chemica Acta, vol. 44, No. 7 (1961), pp. 2151-2153 with translation.
Ali, Fahrenholz and Weinstein, "Simple Method for the Synthesis of Some Boc-Amino Acids", Angew. Chem. Internat. Edit., vol. 11, No. 4, (1972), p. 289.
Guibe-Jampel, Bram, and Vilkas, "Derives `Acyles` du N-Methyl Imidazole", Bull. Soc. Chim. Fr., No. 3 (1973), pp. 1021-1026 with translation.
Bram, "Synthesis de N-tert-Butyloxycarbonyl Aminoacides", Tetrahedron Letters, No. 6 (1973) pp. 469-472 with translation.
Ragnarsson et al., "Tert-Butyloxycarbonyl-L-Proline", Organic Syntheses, vol. 53 (1973), pp. 25-29.
Guibe-Jampel, Bram, Wakselman, and Vilkas, "Water-Soluble Reagents for the Tert-Butoxycarbonylation of Amines", Synthetic Communications, vol. 3, No. 2 (1973), pp. 111-114 with translation.

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