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200517.fm Page 215 Friday, March 18, 2005 2:52 PM
2005
Amino acids
U 0400
Convenient Synthesis and Isolation of 1-Aminocyclopropane-1-carboxylic Acid
and N-Protected ACC Derivatives. — Bisalkylation of imine (I) with diha17- 195 (ACC)
lide (II) installs the cyclopropane ring in a single step. Hydrogenation of the resulting
cyclopropane imine (III) in wet methanol affords the target unprotected amino acid
(IV). N-protected amino acids (VI) and (VIII) are prepared via treatment of the hydrogenation reaction mixture with electrophiles. Due to the high mother liquor losses in
the isolation of imine, a through process is reported for the synthesis of acid (VIII) from
imine (I) with 52% overall yield. — (ALLWEIN*, S. P.; SECORD, E. A.; MARTINS,
A.; MITTEN, J. V.; NELSON, T. D.; KRESS, M. H.; DOLLING, U. H.; Synlett 2004,
14, 2489-2492; Merck Res. Lab., Dep. Process Res., Merck & Co., Inc., Wayne,
PA 19087, USA; Eng.) — Klein
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