A new synthetic route of 1-Tridecanol

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,112-70-9, its application will become more common.

Reference of 112-70-9, Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps,and cheap raw materials. 112-70-9, name is 1-Tridecanol. A new synthetic method of this compound is introduced below.

General procedure: To a solution of 2 (a salt of triethylamine,150mg) in pyridine (5ml), bis(2-oxo-3-oxazolidinyl)phosphinic chloride(120mg, 0.55mmol) and tridecan-1-ol (100 mg, 0.5mmol) were added andthe resulting mixture was stirred overnight at room temperature. The resultingsolution was concentrated to give a residue, which was extracted with CHCl3.The organic solution was washed with water and then concentrated. Theresidue obtained was purified by column chromatography (10:1 CHCl3-MeOH) to give the 500-N-Boc-protected intermediate of 5c (95mg, 62% fromcaprazene) as a colorless solid. Then, the solid was dissolved in a methanolsolution of 80% trifluoroacetic acid (2.7ml) and the solution was kept at roomtemperature for 1 h. The reaction solution was concentrated and diethyl etherwas added to the resulting syrup. The precipitate obtained was thoroughlywashed with diethyl ether and dried to give the colorless solid 5c (110mg,59% as an addition salt of bis-trifluoroacetic acid from caprazene).ESI-MS: m/z 740.4 (MH) ; [a]D19501 (c 0.5, H2O); 1H NMR(500MHz, DMSO-d6) d 0.86 (3H, t, J7Hz, CH3(CH2)12-), 1.20-1.30(20H, m, CH3(CH2)10CH2CH2-), 2.36 (3H, br s, 500 0-NCH3), 2.96 (3H, s,800 0-NCH3), 5.09 (1H, s, 100-H), 5.53 (1H, d, J2Hz, 10-H), 5.64 (1H, d,J8Hz, 5-H), 6.73 (1H, t, J7Hz, 3000-H), 7.63 (1H, d, J8Hz, 6-H), 11.33(1H, s, 3-NH). Anal. calc. for C35H57N5O12 2CF3COOH 3H2O: C 45.84, H6.41, N 6.85. Found: C 45.68, H 6.04, N 6.56.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,112-70-9, its application will become more common.

Reference:
Article; Takahashi, Yoshiaki; Igarashi, Masayuki; Miyake, Toshiaki; Soutome, Hiromi; Ishikawa, Kanae; Komatsuki, Yasuhiro; Koyama, Yoshiko; Nakagawa, Naoko; Hattori, Seiko; Inoue, Kunio; Doi, Norio; Akamatsu, Yuzuru; Journal of Antibiotics; vol. 66; 3; (2013); p. 171 – 178;,
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