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0042372397
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note
-
(2-Pyridyl)dehydroamino acid derivatives 1a-b were prepared from commercially available pyridine-2-carboxaldehyde and 5-bromo-pyridine-2-carboxaldehyde, respectively, in 78-89% yield by treatment with N-(benzyloxycarbonyl)phosphonoglycine trimethyl ester in the presence of N,N,N′,N′-tetramethylguanidine (TMG) in THF at room temperature for 6 h.
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33745336054
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41
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0041871413
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note
-
19F NMR.
-
-
-
-
42
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0041370646
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-
note
-
The absolute configuration of the newly generated chiral center in 4a using (R,R)-6 catalyst was determined to be (5) by cleavage of protective groups to the corresponding known α-amino acid and comparison of its rotation; see: ref 9a.
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44
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0013669499
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For synthesis of azatyrosine [(5-hydroxy-2-pyridyl)glycine], see: (a) Norton, S. J.; Skinner, C. G.; Shive, W. J. Org. Chem. 1970, 26, 1495-1498.
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49
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0030571302
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(e) Coopre, M. S.; Seton, A. W.; Stevens, M. F. G.; Westwell, A. D. Bioorg. Med. Chem. Lett. 1996, 6, 2613-2616.
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51
-
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0041370657
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note
-
The enantiomeric excess (% ee) of (5)-(-)-10 before and after crystallization was determined by converting to Mosher's amide in three steps: see ref 18 for details.
-
-
-
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52
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0041871418
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note
-
Preparative reversed phase HPLC was carried out on a Waters, Symmetry, C18, 7.0 μ, 40 × 100 mm column using 2:98 MeCN/0.1% aqueous trifluoroacetic acid. 25 mL/min at 225 nm.
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