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0343269040
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note
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Ultimately the absolute stereochemistry was proven when an X-ray structure of palinavir dihydrochloride was obtained with material which was identical in all aspects with the one described here, see ref. 9b.
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32
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0342399472
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and references cited therein
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ß-Methyl L-aspartate hydrochloride was purchased from Omega Chemicals, Québec city or was readily prepared from thionyl chloride and L-aspartic acid in methanol. See: Khosla, M. C.; Smeby, R. R. and Bumpus, F. M. Ind. J. Chem. 1967, 5 (6), 279 and references cited therein.
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33
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0343704693
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note
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Three equivalents of sodium methoxide were required for optimal results in this transformation. Use of fewer equivalents of sodium methoxide or use of other bases i.e. : NaH, KH, KO-t-Bu, LiHMDS, NaHMDS, or KHMDS all resulted in lower yields.
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0011267872
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35
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0343269036
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note
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(R)-(-)-1-indanol and (S)-(+)-1-indanol were purchased from Aldrich Chemical Co. The (R)-(-) enantiomer was found to have an ee of 99.8% and the (S)-(+) enantiomer was found to have an ee of 99.7%. These ee's were obtained by HPLC analysis using a Daicel chiral pak AS 4.6 × 250 mm column, eluent: 10% EtOH/hexane isocratic at 0.5 mL/min., PDA detector at 205 nm.
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37
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0342399471
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note
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R for the (R)-indanyl ester : 13.5 min (detection limit <0.5%).
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