Process for the efficient preparation of N-substituted dehydroam

Details Process for the efficient preparation of N-substituted dehydroam Process for the efficient preparation of N-substituted dehydroam

1994-11-17

1996-09-24

Shippen, Michael L.

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

Organic compounds

Carboxylic acid esters

554112, 560 41, C07C22900

Patent

active

055592686

ABSTRACT:
A process for the preparation of N-substituted dehydroamino acid esters by contacting a .beta.-hydroxy-.alpha.-amino acid ester or N- or O-substituted .beta.-hydroxy-.alpha.-amino acid ester with an excess of acetic anhydride and a base is disclosed.

REFERENCES:
patent: 2449191 (1948-09-01), Behrens
patent: 2460708 (1949-02-01), Mozingo
M. Burk et al., Preparation and Use of C.sub.2 -Symmetric Bis(phospholanes): Production of .alpha.-Amino Acid Derivatives via Highly Enantioselective Hydrogenation Reactions, J. Am. Chem. Soc., 115, 10125, (1993).
D. Schluter et al., Reactivity of N-acetyl-3-O-p-tolylsulfonyl-DL-serine methyl ester: nucleophilic displacement by water at C-3 versus elimination, Carbohydrate Research, 38, 333, (1974).
A. Srinivasen et al., Conversion of Threonine Derivatives to Dehydroamino Acids by Elimination of .beta.-Chloro and O-Tosyl Derivatives, J. Org. Chem., 42, 2256 (1977).
I. Photaki, Transformation of Serine to Cysteine. .beta.-Elimination Reactions in Serine Derivatives, J. Am. Chem. Soc., 85, 1123, (1963).
A. Brown et al., Symthesis of (.+-.)-Versimide [Methyl .alpha.-(Methylsuccinimido)acrylate] and Related Compounds, J. Chem. Soc., Perkin Trans. 1, 65, (1972).
C. Balsamini et al., Stereospecific Synthesis of N-(Diphenylmethylene)-.alpha.-,.beta.-didehydroamino Acid Methyl Esters from .beta.-Hydroxy-.alpha.-amino Acids, Synthesis, 779, (1990).
R. Andrusziewicz et al., Dehydration of .beta.-Hydroxyamino Acids with N,N'-Carbonyldiimidazole, Synthesis, 968, (1982).
L. Somekh et al., Stereospecific Synthesis of .alpha.,.beta.-Dehydroamino Acids from .beta.-Hydroxy .alpha.-Amino Acid Derivatives, J. Org. Chem., 48, 907, (1983).

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