Synthesis of N-protected-.alpha.-substituted-glycine racemic est

Details Synthesis of N-protected-.alpha.-substituted-glycine racemic est Synthesis of N-protected-.alpha.-substituted-glycine racemic est

1994-04-13

1996-04-16

Rollins, John W.

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

Organic compounds

Carboxylic acid esters

560115, 560157, 435280, C07C26904, C07C27112

Patent

active

055084664

ABSTRACT:
A method is described for synthesis of N-Boc-L-propargylglycine, a key intermediate used in the preparation of high-potency, orally-active renin inhibitors. This method involves reaction of an organic halide with a glycine cation equivalent, such as methyl N-Boc-2-acetoxyglycine, in the presence of zinc dust to give Boc-protected amino acid derivatives in high yield. Typically useful organic halides are allylic, benzylic and propargylic halides. Resolution of methyl N-Boc-propargylglycine with .alpha.-chymotrypsin provides N-Boc-L-propargylglycine in high yield.

REFERENCES:
patent: 3878043 (1975-04-01), Matta et al.
patent: 3884958 (1975-05-01), Holden et al.
patent: 3920730 (1975-11-01), Gleason et al.
patent: 3994954 (1976-11-01), Gleason et al.
patent: 3997584 (1976-12-01), Gleason et al.
patent: 4108854 (1978-08-01), Gleason et al.
patent: 4439524 (1984-03-01), Schutt
patent: 4716113 (1987-12-01), Urban
patent: 5212185 (1993-05-01), Hanson
patent: 5223535 (1993-06-01), Hanson et al.
patent: 5227401 (1993-07-01), Hanson et al.
patent: 5246969 (1993-09-01), Hanson et al.
patent: 5252591 (1993-09-01), Hanson et al.
Burdick & Jackson (1982) High Purity Solvent Guide, 2nd Ed. Burdick & Jackson Laboratories, Inc., Muskegon, MI, pp. 128-137.
Taguchi et al. (1988) Tetrahed. Lett., 29(41), 5291-5294.
Williams et al. (1990) J. Org. Chem., 55, 4657-4663.
Schricker et al. (1992) Biorg. Med. Chem. Lett., 2(5), 387-390 in Chem Abst, 119, Abst. #96107.
Abood et al. (1994) Tetrahed. Lett., 35 (22), 3669-3672.
Schwicker et al. (1992) Bioorg. Med. Chem. Lett., 2(5), ".gamma.-Chymotrypsin Catalyzed Enantioselective Hydrolysis of Alkenyl-.gamma.-Amino Acid Esters", pp. 387-390.
W. N. Speckamp et al., J. Org Chem., 58, 3259-3268 (1993).
P. Munster et al., Synthesis, 223-225 (1987).
H. H. Mooiweer et al., Tetrahedron, 45, 4627-4636 (1989).
O. Leukart et al., Helv. Chem. Acta., 59, 2181-2183 (1976).

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