N,N-Dimethylformamide di-tert-butyl acetal is used as a reagent in the synthesis of (S)-2-(1-tert-butoxycarbonyl-2-{4-[2-(5-methyl-2-phenyloxazol-4-yl)ethoxy]phenyl}ethylamino)benzoic acid methyl ester, 3-O-tert-butylmorphine, tert-butylesters of pyrrole and indolecarboxylic acids. Further, it is used in the preparation of indolizines by intermolecular cyclization of picolinium salts.
This Thermo Scientific Chemicals brand product was originally part of the Alfa Aesar product portfolio. Some documentation and label information may refer to the legacy brand. The original Alfa Aesar product / item code or SKU reference has not changed as a part of the brand transition to Thermo Scientific Chemicals.
Aplicaciones
El acetal de di-terc-butilo de N,N-Dimetilformamida se utiliza como reactivo en la síntesis del éster metílico del ácido (S)-2-(1-terc-butoxicarbonil-2{4-[2-(5-metil-2-feniloxazol-4-il)etoxi]fenil}etilamino)benzoico, la 3-O-terc-butilmorfina y los terc-butilésteres de ácidos pirrol e indolcarboxílicos. Además, se utiliza en la preparación de indolizinas por ciclización intermolecular de sales de picolinio.
Solubilidad
Miscible con tolueno y benceno.
Nota
Sensible a la humedad. Incompatible con ácidos y agentes oxidantes fuertes.
RUO – Research Use Only
General References:
- The conversion of carboxylic acids to their esters using DMF acetals (see for example, N,N-Dimethyl formamide dimethyl acetal, A15350 ) can be extended to the preparation of t-butyl esters by using excess reagent in benzene or toluene as solvent: Synthesis, 135 (1983).
- Gatineau, D.; Nguyen, D. H.; Hérault, D.; Vanthuyne, N.; Leclaire, J.; Giordano, L.; Buono, G. H-adamantylphosphinates as universal precursors of P-stereogenic compounds. J. Org. Chem. 2015, 80 (8), 4132-4141.
- Hoecker, J.; Liffert, R.; Burch, P.; Wehlauch, R.; Gademann, K. Caged retinoids as photoinducible activators: Implications for cell differentiation and neurite outgrowth. Org. Biomol. Chem. 2013, 11 (20), 3314-3321.