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1. 发明公开

EP2448917A2 VERFAHREN ZUR ENANTIOSELEKTIVEN ADDITION VON ORGANOMETALLISCHEN KOHLENSTOFFNUKLEOPHILEN AN TRIFLUORMETHYLKETONE UND VERWENDUNG DES VERFAHRENS IN DER SYNTHESE VON HIV REVERSE TRANSCRIPTASE INHIBITOREN 审中-公开
标题翻译：方法不对称加成有机金属碳亲核试剂的TO三氟甲基酮及其程序USE IN HIV逆转录酶抑制剂的合成
公开(公告)号：EP2448917A2
公开(公告)日：2012-05-09
申请号：EP10728609.8
申请日：2010-06-25
申请人： Archimica GmbH
发明人： NONNENMACHER, Michael , JUNG, Jörg , MEUDT, Andreas
IPC分类号： C07C243/08 , C07D265/18 , C07C215/70
CPC分类号： C07D265/18 , C07B2200/07 , C07C213/00 , C07C2601/02 , Y02P20/55 , C07C215/70
摘要： The invention relates to a method for producing compounds of the formula A1, wherein the carbon atom to which both the CF3 group and the hydroxy group are bonded is a stereocenter having either the R or the S configuration and wherein R1 and R2 are a C1-C8 alkyl, C3-C8 cycloalkyl, C2-C8 alkenyl, C4-C8 cycloalkenyl, C2-C8 alkynyl, C6-C14 aryl, or C5-C13 heteroaryl group independently of each other, wherein the alkyl, alkenyl, and alkynyl groups are straight-chained or branched and wherein all stated groups are unsubstituted or are mono- or polysubstituted with the same or different substituents selected from the group: halide, NO
2 , SO
3 H, SO
3 Na, SO
3 K, CN, OH, NH
2 , NH-lower alkyl, N-di-lower alkyl, COOH, COO-lower alkyl, lower alkyl, and C3-C6 cycloalkyl, and wherein terminal OH-, NH
2 -, and NH-lower alkyl groups and acidic H atoms are unprotected or are protected with a protective group, wherein a mixture of a zinc(II) salt, an enantiomerically pure or enantiomerically enriched auxiliary of the formula (I), wherein R3 and R4 are C6-C14 aryl, C5-C13 heteroaryl, C1-C8 alkyl, or C2-C8 alkenyl groups or hydrogen independently of each other and R5 and R6 are C6-C14 aryl, C5-C13 heteroaryl, C1-C8 alkyl, C2-C8 alkenyl, or C2-C8 alkynyl groups or hydrogen independently of each other or R5 and R6 together represent a C3-C7 alkylene or C3-C7 alkenylene group and at least one of the centers C1, C2, preferably both, is a stereocenter regardless of the configuration of the other center and has either the R or the S configuration and a second auxiliary, which is selected from the group comprising the alcohols, phenols, mercaptans, amines, carboxylic acids, urea derivatives, or the heterocycles containing nitrogen, oxygen, or sulfur, is reacted with an organic or inorganic base and then is reacted with an organometallic compound R1 -M in which R1 has the meaning specified above and in which M is selected from the group: lithium, sodium, potassium, magnesium halide, magnesium cyanide, magnesium-lower alkyl-alcoholates, and then is reacted with a trifluoromethyl ketone (II), wherein R2 has the meaning stated above.
摘要翻译：本发明涉及一种用于制备式A1的化合物，worin到其中两个CF 3基团和羟基基团所结合的碳原子是具有R或S构型和worin R1和R2是一个C1立体中心 C8烷基，C3-C8环烷基，C2-C8链烯基，C4-C8环烯基，C2-C8炔基，C6-C14芳基，或海誓山盟的C5-C13杂芳基unabhängig，worin烷基，烯基和炔基是直 -chained或支链的并且worin都表示基团是unsubstituiertem或单或与选自相同或不同的取代基取代：卤素，NO 2，SO 3 H，SO 3 Na或-SO 3 K.，CN，OH，NH 2，NH-低级烷基，N 二 - 低级烷基，COOH，COO - 低级烷基，低级烷基，C3-C6环烷基，和worin末端OH，NH 2和NH - 低级烷基基团和酸性氢原子是未保护的或用保护基保护，worin锌（II）盐的混合物，对映体纯或对映体富集的辅助式（I）的，worin R3和R4是C6-C14芳基，C5-C13杂芳基，C1-C8烷基，或C2-C8烯基或氢彼此独立地和R5和R6是C6-C14芳基，C5 -C13杂芳基，C1-C8烷基，C2-C8烯基或C2-C8炔基或氢彼此独立地或R5和R6一起表示的C3-C7亚烷基或C3-C7亚链烯基和中心的至少一个 C1，C2，优选两者，是立体声中心不管其他中心的构型，并且具有R或S构型和第二辅助，它是从包括以下的组的醇，酚，硫醇，cardamines，羧酸选取全部，脲衍生物，或者含有氮，氧或硫的杂环，是在有机或无机碱反应用，然后在有机金属化合物R1 -M其中R 1进行反应与具有上面和其中M所指定的含义是从所选择的组：锂，钠，钾，卤化镁，镁氰化物，镁 - 低级烷基醇化物，然后进行反应与三氟甲基酮（II），worin R2具有如上所述的含义。

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