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Product Name: Boc Anhydride

Category: Peptide Reagents

CAT No.: 10102


Product Data Sheet

Product Name

Boc Anhydride

CAS No 24424-99-5
Molecular Formula C10H18O5
Molecular Weight 218.25
Appearance Colorless solidified melt or fragments
Melting Point 20~25℃
puriy 99% min.
Packing 50kg/drum.
Storage In cool, dry place
Lead Time In stock

Notes:

Reagent for amino group protection as the t-butyl carbamate (t-butoxycarbonyl, Boc derivatives), in high yield under mild conditions, widely used in peptide chemistry[1,2].
Benzyl carbamates(Cbz, Z) may be transformed into Boc in a one pot procedure catalysed by Pd/C[3] .
Amides can be protected in the presence of a catalytic quantity of DMAP[4,5]; the amide link of the product undergoes facile alkaline hydrolysis or methanolysis. The nitrogen function of indoles and pyrroles can also be protected under similar conditions[6,7]. 1-Boc indoles may be synthesized from N-Boc 2-alkyl aniline [8].
The Boc group is readily cleaved with acid, most often Trifluoroacetic acid.
In the presence of 1 equivalent of DMAP in acetonitrile, arylamines are converted to isocyanates, generally in high yield; the dicarbonate here behaves as a convenient phosgene replacement[9] . The same reagent system has also been applied nitroalkanes for the ambient temperature generation of nitrile oxides which were trapped in situ with dipolarophiles[10] .
Feature on uses of this reagent in synthesis was reveiwed[11].

Ref:

  1. Org.Synthe.Coll., 1990, 7, 70
  2. Synthesis, 223 (1987): Org.Synthe.Coll., 1998, 9, 124, 300
  3. Tetrahedron Lett., 1992, 33, 3167
  4. J. Org.Chem., 1983,48, 2424
  5. Acta Chem. Scand.B, 1986, 40, 745
  6. J.Chem.Soc., Chem. Commun., 1984, 1699
  7. Org.Synth.Coll., 1998, 9, 121
  8. Synthesis, 1991, 871
  9. Angew, Chem.Int.Ed., 1995, 34, 2497
  10. Synthesis, 1997, 309
  11. Synlett, 2001, 1995

 

 
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