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1
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84919066673
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The term “fluoromethyl ketone” is applied generally to mono-, di, and trifluoromethyl ketones.
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5
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37049063607
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344. Studies of trifluoroacetic acid. Part XVIII. Reaction of N-aroylglycines with perfluoro-carboxylic anhydrides
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Although treatment of N-blocked amino acids with acetic anhydride and pyridine results in good yields of the corresponding methyl ketones, similar treatment with trifluoroacetic anhydride (in the presence or absence of catalytic 4-dimethylaminopyridine) affords only ketone products with the unsubstituted amino acid glycine.
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(1961)
Journal of the Chemical Society (Resumed)
, pp. 1771
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Bourne1
Burdon2
McLoughlin3
Tatlow4
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6
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84919092480
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3ZnI useful in the preparation of simple trifluoromethyl ketones au]T. Kitazume, However, the use of such organometallic reagents is problematic in the preparation of peptidyl products.
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(1981)
Chem. Lett.
, pp. 1679
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Ishikawa1
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9
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84919066670
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a 12.4) causing side reactions in the peptide coupling.
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10
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0000206354
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The Sarett oxidation is a chromium trioxide/pyridine oxidation with the active complex generated in situ. In this case double the normal equivalents of pyridine and chromium trioxide and longer reaction times (i.e., 2h, 25°) are necessary to ensure complete oxidation.
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(1953)
J. Am. Chem. Soc.
, vol.75
, pp. 422
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Poos1
Arth2
Beyler3
Sarett4
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11
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0004060828
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The only literature procedures available for the oxidation of trifluoromethyl carbinols employ very harsh conditions which are unsuitable for these peptidyl compounds., 2nd edition, Ellis Horwood Ltd, For examples see
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(1976)
Chemistry of Organic Fluorine Compounds
, pp. 208-213
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Hudlicky1
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12
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84919066669
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If optically active materials were subjected to the oxidation procedure, the following points are pertinent. Method A has been frequently used to oxidize α-chiral aldehydes without racemizatlon, and therefore should proceed in a similar manner for the preparation of optically active mono- and difluoromethyl ketones. In the oxidation of the trifluoromethyl compounds (Method B) since the oxidation is carred out under aqueous conditions, it is hoped that the ketone in its hydrated form will not be prone to racemization, even in base.
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13
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84919066668
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3δ: 22.3, 22.6, 22.9, 24.5, 36.1, 36.4, 41.0, 51.3, 51.7. 56.3, 84. 27, d, J = 185.3Hz), 84.41 (d, J = 183.8Hz), 127.2, 128.7, 129.2, 135.7, 136.1, 170.6, 170.8, 172.9, 173.2, 203.9 (d, J = 17.9Hz).
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14
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84919066667
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Compounds 1a, 1b, and 1c were all specific inhibitors for bovine chymotrypsin, as were compounds 2a and 2b towards porcine pancreatic elastase. Full details of these results will be reported elsewhere.
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