Application of 121496-39-7, A common heterocyclic compound, 121496-39-7, name is tert-Butyl benzyl(2-hydroxyethyl)carbamate, molecular formula is C14H21NO3, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.
TRIPHENYLPHOSPHINE (0.0125 mol) in dry THF (10 mL) was added to BENZYL- (2- hydroxy-ethyl) -carbamic acid tert-butyl ester 111-8 in THF (30 mL) at 0 C under nitrogen via a cannula. Diisopropyl azodicarboxylate (DIPAD) (0. 013 mol) was then added dropwise and the solution was stirred for 20 min at 0 C after the addition of DIPAD. Diphenyl phosphonic azide (DPPA) (0.0125 mol) was added at 0 C and the solution was stirred for 5 h at room temperature (TLC monitor the amount of 111-8). The solution was then concentrated in vacuo and the crude residue was purified by column chromatography to yield azide intermediate (silica gel, hexanes: EtOAc, 9.5 : 0.5). To a solution of above azide intermediate in THF (5 mL) were added Ph3P (0. 012 mol) and water (0.03 mol) at 0 C. THE mixture was stirred 2 h at 0 C and 21 h at room temperature. The solvent was removed under reduced pressure, and the residue was treated with 10 % citric acid (30 ML) and EtOAc (15 mL). The aqueous layer separated was washed EtOAc (10 mL X 2). Then the aqueous layer was basified with 2M NAOH and the alkaline solution was extracted with CH2C12 (30 ML X 3). The extracts were dried over anhydrous MgS04, and the solvent was then removed under reduced pressure to give pure product.
The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. We look forward to the emergence of more reaction modes in the future.
Reference:
Patent; NORTHWESTERN UNIVERSITY; WO2005/26111; (2005); A2;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics