1438852-72-2Relevant articles and documents
Determination of the absolute configuration of (+)- and (?)-N-CBZ-3-fluoropyrrolidine-3-methanol using vibrational circular dichroism and confirmation of stereochemistry by conversion to (R)-tert-butyl 3-fluoro-3-(((R)-1-phenylethyl)carbamoyl)pyrrolidine-1-carboxylate
Procopiou, Panayiotis A.,Hatley, Richard J.D.,Lynn, Sean M.,Copley, Royston C.B.,He, Yanan,Minick, Douglas J.
, p. 1222 - 1230 (2016)
Racemic N-CBZ-3-fluoropyrrolidine-3-methanol (±)-1 was resolved by preparative chiral HPLC. The absolute configuration of the enantiomers of 1 was identified by vibrational circular dichroism and confirmed by chemical synthesis, which involved exchanging the CBZ protecting group of (?)-1 with Boc, followed by oxidation with RuCl3, NaIO4, activation of the resulting acid with carbonyl diimidazole and reaction with (R)-α-methylbenzylamine to give (R)-tert-butyl 3-fluoro-3-(((R)-1-phenylethyl)carbamoyl) pyrrolidine-1-carboxylate 7. The latter was compared with authentic (S)-tert-butyl 3-fluoro-3-(((R)-1-phenylethyl)carbamoyl)pyrrolidine-1-carboxylate 6 and its diastereomer 7; the configuration of diastereomer 6 was obtained by an X-ray diffraction study. This established that the enantiomer (?)-1 had an (R)-configuration.
NOVEL COMPOUNDS
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Page/Page column 42, (2016/06/06)
A compound of formula (I): being 4-(3-Fluoro-3-(2-(5, 6, 7, 8-tetrahydro-l, 8-naphthyridin-2-yl) ethyl) pyrrolidin-l-yl)-3-(3-(2-methoxyethoxy) phenyl) butanoic acid, or a salt thereof.
CYTOTOXIC PEPTIDES AND ANTIBODY DRUG CONJUGATES THEREOF
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Page/Page column 198, (2013/06/05)
The present invention is directed to cytotoxic pentapeptides, to antibody drug conjugates thereof, and to methods for using the same to treat cancer.