Some common heterocyclic compound, 1092522-02-5, name is tert-Butyl (4-aminophenyl)(methyl)carbamate, molecular formula is C12H18N2O2, 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. HPLC of Formula: C12H18N2O2
General procedure: HBTU (1.82g, 3.59mmol), DIPEA (0.84mL, 4.80mmol) and monomethyl suberate (0.93mL, 5.28mmol) were added to a solution of 34 (1.0g, 4.80mmol) in DMF (10mL) and the mixture was stirred for 12hat rt. Then the reaction was quenched with H2O and extracted using EtOAc, dried over MgSO4 and passed through a filter column to give corresponding ester which was dissolved in the minimum amount of dioxane. H2O with pH adjusted to 3 using 3N HCl was added and the reaction mixture was stirred at reflux overnight to yield the corresponding free amine. The reaction was basified and extracted using EtOAc, then dried, concentrated and passed through a filter column to give the free amine. To a solution of this free amine (1.0g, 3.59mmol) in DMF (10mL) was added HBTU (1.36g, 3.59mmol), DIPEA (0.66mL, 3.59mmol) and 1,4-dibenzyloxy-5-isopropyl benzoic acid (0.76g, 4.31mmol) and the solution was stirred for 12hat 80C. The reaction mixture was quenched with H2O and extracted with EtOAc (25mL¡Á3). The combined organic layer was collected, dried over anhydrous MgSO4 and concentrated under reduced pressure to give a light yellow residue, which was purified by silica gel chromatography (EtOAc:n-hexane=1: 1) to give 42 as a colorless liquid in 65% yield (overall from 34)
These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1092522-02-5, its application will become more common.
Reference:
Article; Mehndiratta, Samir; Lin, Mei-Hsiang; Wu, Yi-Wen; Chen, Chun-Han; Wu, Tung-Yun; Chuang, Kuo-Hsiang; Chao, Min-Wu; Chen, Yi-Ying; Pan, Shiow-Lin; Chen, Mei-Chuan; Liou, Jing-Ping; European Journal of Medicinal Chemistry; vol. 185; (2020);,
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