6-[[(2S)-3-Chloro-2-hydroxypropyl]oxy]-2(1H)-quinolinone -Drug Synthesis Database

【结构式】

【分子编号】13918

【品名】6-[[(2S)-3-Chloro-2-hydroxypropyl]oxy]-2(1H)-quinolinone

【CA登记号】

【分子式】C₁₂H₁₂ClNO₃

【分子量】253.68492

【元素组成】C 56.82% H 4.77% Cl 13.98% N 5.52% O 18.92%

与该中间体有关的原料药合成路线共 1 条

合成路线1

该中间体在本合成路线中的序号：(III)

The synthesis of the (+)-(R)-isomer of OPC-18790 has been published: The condensation of 6-hydroxyquinolin-2(1H)-one (I) with (S)-(+)-epichlorohydrin (II) by means of triethylamine in methanol gives (S)-(+)-6-(3-chloro-2-hydroxypropoxy)quinolin-2(1H)-one (III), which by reaction with KOH in isopropanol/water yields the (R)-(-)-epoxide (IV). Finally, this compound is condensed with 3,4-dimethoxybenzylamine (V) by heating its mixture at 80 C. The (+)-(R)-isomer is about 10-fold more potent than the (-)-(S)-isomer.

参考文献中间体

合成目标

【1】 Fujioka, T.; Teramoto, S.; Tominaga, M.; Mori, T.; Sumida, T.; Yabuuchi, Y.; Tsujimi, S.; Takemoto, K.; Hosokawa, T.; Synthesis and biological activities of optically active 6-[3-(3,4-dimethox ybenzylamino)-2 hydroxypropoxy]-2(1H)-quinolinone (OPC-18790). Chem Pharm Bull 1996, 44, 8, 1596.

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
(I)	13913	6-Hydroxy-2(1H)-quinolinone		C₉H₇NO₂	详情	详情
(II)	13917	(S)-Epichlorohydrin; (2S)-2-(Chloromethyl)oxirane;(S)-(+)-epichlorohydrin	67843-74-7	C₃H₅ClO	详情	详情
(III)	13918	6-[[(2S)-3-Chloro-2-hydroxypropyl]oxy]-2(1H)-quinolinone		C₁₂H₁₂ClNO₃	详情	详情
(IV)	13919	6-[(2R)Oxiranylmethoxy]-2(1H)-quinolinone		C₁₂H₁₁NO₃	详情	详情
(V)	13920	(3,4-Dimethoxyphenyl)methanamine; 3,4-Dimethoxybenzylamine; Veratrylamine	5763-61-1	C₉H₁₃NO₂	详情	详情

Extended Information