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【结 构 式】

【分子编号】24980

【品名】methyl 7-(hydroxymethyl)-2-naphthoate

【CA登记号】

【 分 子 式 】C13H12O3

【 分 子 量 】216.23648

【元素组成】C 72.21% H 5.59% O 22.2%

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:(II)

Synthesis of intermediate (V) of DX-9065a: Compound (V) has been obtained as follows: The reaction of 7-methoxy-1,2,3,4-tetrahydronaphthalen-2-one (VII) with trimethylsilyl cyanide using BF3 ethearate as catalyst gives 7-methoxy-3,4-dihydronaphthalene-2-carbonitrile (VIII), which is aromatized with sulfur and Pd/C to naphthalene (IX). The demethylation of (IX) with BBr3 in dichloromethane affords 7-hydroxynaphthalene-2-carbonitrile (X), which is finally converted into the triflate (V) with PhN(SO2CF3)2 as triflating agent. Alternatively, the triflation of 7-methoxy-2-naphthol (XI) as before gives the triflate (XII), which is converted into the previously obtained carbonitrile (IX) by reaction with Zn(CN)2 catalyzed by triphenylphosphine and palladium acetate in hot 1-methyl-2-pyrrolidone.

1 Bauman, J.G.; Xu, W.; May, K.B.; Guilford, W.J.; Morgan, T.K. Jr.; Wu, S.C.; Yan, S.-X.; Morrissey, M.M.; Practical laboratory-scale synthesis of the factor Xa inhibitor DX-9065a. 215th ACS Natl Meet (March 29 1998, Dallas) 1998, Abst MEDI 131.
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) 24979 dimethyl 2,7-naphthalenedicarboxylate C14H12O4 详情 详情
(II) 24980 methyl 7-(hydroxymethyl)-2-naphthoate C13H12O3 详情 详情
(III) 24981 7-(hydroxymethyl)-2-naphthamide C12H11NO2 详情 详情
(IV) 24982 7-(chloromethyl)-2-naphthonitrile C12H8ClN 详情 详情
(V) 24983 [(7-cyano-2-naphthyl)methyl](triphenyl)phosphonium chloride C30H23ClNP 详情 详情
Extended Information