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Reagent for the introduction of the Boc protecting group.Di-tert-butyl dicarbonate is a reagent used for the introduction of BOC protecting group. It plays an important role in the preparation of 6-acetyl-1,2,3,4-tetrahydropyridine by reacting with 2-piperidone. It serves as a protecting group used in solid phase peptide synthesis.
Reagent for amino group protection as the tert-butyl carbamate (tert-butoxycarbonyl, Boc derivatives), in high yield under mild conditions, widely used in peptide chemistry; see Appendix 6. For practical details, literature references and tabulated results, see: Org. Synth. Coll., 7, 70 (1990). For further examples see: Synthesis, 223 (1987): Org. Synth. Coll., 9, 124, 300 (1998). Benzyl carbamates (Cbz, Z) may be transformed into Boc in a one pot procedure catalyzed by Pd/C: Tetrahedron Lett., 33, 3167 (1992).
Rapid and efficient formation of Boc derivatives of amines, catayzed by Copper(II) tetrafluoroborate hexahydrate, 26127 has been described: Tetrahdron Lett., 47, 1087 (2006).
For Boc protection of phenols, alcohols, thiols etc. under phase-transfer conditions, see: Can. J. Chem., 63, 153 (1985).
Amides can be protected in the presence of a catalytic quantity of DMAP ( 4-(Dimethylamino)pyridine, A13016 ): J. Org. Chem., 48, 2424 (1983); Acta Chem. Scand. B, 40, 745 (1986); 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: J. Chem. Soc., Chem. Commun., 1699 (1984); Org. Synth. Coll., 9, 121 (1998). 1-Boc indoles may be synthesized from N-Boc 2-alkylanilines: Synthesis, 871 (1991).
The Boc group is readily cleaved with acid, most often Trifluoroacetic acid, L06374 .
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: Angew. Chem. Int. Ed., 34, 2497 (1995). The same reagent system has also been applied to nitroalkanes for the ambient temperature generation of nitrile oxides which were trapped in situ with dipolarophiles: Synthesis, 309 (1997). Carboxylic acids can be esterified in the presence of a catalytic amount of DMAP: Synlett, 263 (2004).
Carboxylic acids have also been converted to Boc-protected amines, via a one-pot Curtius rearrangement, using the reagent in the presence of sodium azide, with catalytic amounts of TBAB and zinc triflate: Org. Lett., 7, 4107 (2005).
For a brief feature on uses of the reagent in synthesis, see: Synlett, 1995 (2001).
Hong, X.; Wang, H.; Liu, B.; Xu, B. Ruthenium-catalyzed double-fold C-H tertiary alkoxycarbonylation of arenes using di-tert-butyl dicarbonate. Chem. Commun. 2014, 50 (91), 14129-14132.
Sweis, R. F.; Wang, Z.; Algire, M.; Arrowsmith, C. H.; Brown, P. J.; Chiang, G. G.; Guo, J.; Jakob, C. G.; Kennedy, S.; Li, F.; Maag, D.; Shaw, B.; Soni, N. B.; Vedadi, M.; Pappano, W. N. The Discovery of A-893, A New Cell-Active Benzoxazinone Inhibitor of Lysine Methyltransferase SMYD2. ACS Med. Chem. Lett. 2015, 6 (6), 695-700.
Hazard Statements: H228-H315-H317-H318-H330-H335-H500
Flammable solid. Causes skin irritation. May cause an allergic skin reaction. Causes serious eye damage. Fatal if inhaled. May cause respiratory irritation. May form combustible dust concentrations in air
Precautionary Statements: P210-P240-P241-P260-P264b-P271-P272-P280-P284-P302+P352-P304+P340-P305+P351+P338-P310-P312-P333+P313-P362-P370+P378q-P501c
Keep away from heat/sparks/open flames/hot surfaces. - No smoking. Ground/bond container and receiving equipment. Use explosion-proof electrical/ventilating/lighting/ equipment. Do not breathe dust/fume/gas/mist/vapours/spray. Wash face, hands and any exposed skin thoroughly after handling Use only outdoors or in a well-ventilated area. Contaminated work clothing should not be allowed out of the workplace. Wear protective gloves/protective clothing/eye protection/face protection. Wear respiratory protection. IF ON SKIN: Wash with plenty of soap and water. 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. Call a POISON CENTER or doctor/physician if you feel unwell. If skin irritation or rash occurs: Get medical advice/attention. Take off contaminated clothing and wash before reuse. In case of fire: Use CO2, dry chemical, or foam Dispose of contents/ container to an approved waste disposal plant