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Bis(2-oxo-3-oxazolidinyl)phosphinic chloride was used in the preparation of hexadepsipeptide. Also used as reagent is used for activating the carboxylic group, synthesis of amides, esters and peptides.
T Miyazawa; T Donkai; T Yamada; S Kuwata. Effect of copper(II) chloride on suppression of racemization in peptide synthesis by the mixed anhydride and related methods. International Journal of Peptide and Protein Reseach. 1992, 40 (1), 49-53.
H T Le; J F Gallard; M Mayer; E Guittet; R Michelot. Use of BOP-Cl in the presence of Boc-amino monothioacids for the thioacylation of imino acid residues. Bioorganic & Medicinal Chemistry. 1996, 4(12), 2201-2209.
Coupling reagent for which the rates of reaction with various nucleophiles are sufficiently different to permit a genuine "one-step" coupling of carboxylic acids with amines: Synthesis, 547 (1980). Particularly suitable for coupling N-alkyl amino acids: J. Org. Chem., 51, 3350 (1986). For discussion of strategies for one-step coupling in synthesis of amides, see: Synthesis, 413 (1984), and of the scope and limitations of the reagent in peptide coupling, see: Int. J. Pept. Prot. Res., 29, 574 (1987); J. Org. Chem., 55, 2895 (1990). See also Appendix 6.
For use in the direct selective 5'-acylation of nucleosides by carboxylic acids, (without 3'-protection), see: Tetrahedron, 44, 229 (1988). For high yield dehydration of carboxylic acids to anhydrides, see: Synthesis, 616 (1981). Also used in macrolide cyclization: J. Am. Chem. Soc., 104, 6818 (1982), and in formation of acyclic esters: Synth. Commun., 14, 515 (1984).
The mixed anhydride formed with carboxylic acids adds to imines to give ß-lactams: Synthesis, 63 (1982):
These are also formed in high yield by cyclization of ß-amino acids: Bull. Korean Chem. Soc., 12, 457 (1991).
Mentions de danger (UE): H314
Causes severe skin burns and eye damage.
Mentions de prudence: P260-P264b-P280-P301+P330+P331-P303+P361+P353-P304+P340-P305+P351+P338-P310-P363-P501c
Do not breathe dust/fume/gas/mist/vapours/spray. Wash face, hands and any exposed skin thoroughly after handling Wear protective gloves/protective clothing/eye protection/face protection. IF SWALLOWED: Rinse mouth. Do NOT induce vomiting. IF ON SKIN (or hair): Remove/Take off immediately all contaminated clothing. Rinse skin with water/shower. IF INHALED: Remove to fresh air and keep at rest in a position comfortable for breathing. IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. Immediately call a POISON CENTER or doctor/physician. Wash contaminated clothing before reuse. Dispose of contents/ container to an approved waste disposal plant