Adding a certain compound to certain chemical reactions, such as: 87905-98-4, name is Benzyl (5-hydroxypentyl)carbamate, belongs to amides-buliding-blocks compound, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound 87905-98-4, category: amides-buliding-blocks
To a solution of oxalyl chloride (814 mul, 9.62 mmol, 2.3 equiv.) in dried dichloromethane (25 ml) under an inert atmosphere was slowly added a solution of dimethylsulfoxyde (1.3 ml, 18.2 mmol, 4.3 equiv.) in dried dichloromethane (10 ml). The solution was stirred for 5 min at -70C then a suspension of benzyl ((5-hydroxypentyl)carbamate) [21] (1 g, 4.22 mmol, 1 equiv.) in dried dichloromethane (25 ml) was transferred via canula. The mixture was stirred for 25 min at -70C then triethylamine (11.7 ml, 8.44 mmol, 20 equiv.) was slowly added. The reaction mixture was stirred for 20 min at -70C and 15 min at room temperature and then quenched by addition to 600 ml of water. The aqueous phase was extracted with diethylether (3×100 ml) and the combined organic layers were dried over magnesium sulfate, filtered and concentrated to dryness under reduced pressure to obtain the aldehyde (1.1 g) used in the next step without purification. To a suspension of potassium cyanide (249 mg, 3.83 mmol, 1 equiv.) in water (520 mul) were added ammonium chloride (203 mg, 3.83 mmol, 1 equiv.) and ammonium hydroxide 33% (1.32 ml; 20.3 mmol, 5.3 equiv.). The reaction mixture was stirred for 15 min at 0C then a solution of the aldehyde (900 mg, 3.83 mmol, 1 equiv.) in dioxane (1.35 ml) was added dropwise over 20 min. The mixture was stirred for 20 h and then quenched by addition of water (10 ml) and diethyl ether (30 ml). The aqueous phase was acidified with HCl 1 M (50 ml), washed with diethyl ether (3×20 ml), basified to pH = 12 with NaOH 1 M (20 ml) and then extracted with dichloromethane (4×10 ml). The combined organic layers were dried over magnesium sulfate, filtered and concentrated to dryness under reduced pressure to obtain the protected aminonitrile; yield: 905 mg (91%). 1H NMR (MeOD-d4, 300 MHz) delta 1.52 (m, 4H, H4, H5), 1.71 (m, 2H, H3), 3.14 (t, 2H, H6), 3.71 (t, 2H,H2), 5.06 (s, 2H, H8), 7.34 (m, 5H, H10-H12); 13C NMR (MeOD-d4, 75 MHz) . 23.9 (C4), 30.4 (C5), 35.9 (C3), 41.5 (C6), 44.2 (C2), 67.4(C8), 123.1 (C1), 128.8-129.6 (C10-C12), 138.6 (C9), 159.0 (C7) (seeSI, Figs. S3 and S4).
At the same time, in my other blogs, there are other synthetic methods of this type of compound, Benzyl (5-hydroxypentyl)carbamate, and friends who are interested can also refer to it.
Reference:
Article; Bordier, Franck; Stam, Mark; Darii, Ekaterina; Tricot, Sabine; Fossey, Aurelie; Rohault, Johanna; Debard, Adrien; Mariage, Aline; Pellouin, Virginie; Petit, Jean-Louis; Perret, Alain; Vallenet, David; Salanoubat, Marcel; Weissenbach, Jean; Vergne-Vaxelaire, Carine; De Berardinis, Veronique; Zaparucha, Anne; Journal of Molecular Catalysis B: Enzymatic; vol. 107; (2014); p. 79 – 88;,
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