A practical preparation of diisopropyl phosphoryl protected amino acids

Tetrahedron Letters

Volumn 39, Issue 52, 1998, Pages 9583-9586

  Brands, K M J ^a   Wiedbrauk, K ^a   Williams, J M ^a   Dolling, U H ^a   Reider, P J ^a  

^a MERCK RESEARCH LABORATORIES   (United States)

Author keywords

Amino acids and derivatives; Phosphoramidates; ProteCting groups

Indexed keywords

AMINO ACID DERIVATIVE; DIISOPROPYLPHOSPHITE; HYPOCHLORITE SODIUM; N (O,O DIISOPROPYLPHOSPHORYL) 4 HYDROXYPROLINE; PHOSPHORUS DERIVATIVE; SODIUM HYDROXIDE; UNCLASSIFIED DRUG;

ARTICLE; DRUG SYNTHESIS; PH; PROTECTION;

EID: 0032564548     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)02300-4     Document Type: Article

References (15)

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10. 7. Yin, Y.-W.; Chen, B.-M.; Xue, C.-B.; Zhao, Y.-F. Phosphorous and Sulfur, 1988, 39, 131-138.
11. 8. The pKa of diethylphosphite in water has been reported to be 13.0 by Guthrie, J.P. Can. J. Chem., 1979, 57, 236-239.
12. 9. Diisopropylphosphite was purchased from Strem Chemicals Inc..
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14. 11. Li, Y.-C.; Zhao, Y.F. Phosphorous, Sulfur, Silicon Rel. Elem., 1991, 60, 233-237.
15. 12. The methyl ester of (S)-(+)-DIPP-phenylglycine was prepared by treatment of the carboxylic acid with an excess of trimethylsilyldiazomethane. The resulting crude product was analyzed by Supercritical Fluid Chromatography (SFC) using a Chiralcel OF (0.46×25 cm) column (Daicel Chemical Industries). Conditions: 300 bar pressure; 35°C oven temperature; 1.0 mL/min total flowrate; 5.0% of methanol as modifier.; DAD detection at 205 nm.