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【结 构 式】

【分子编号】25643

【品名】N-hydroxy-3-[(4-methoxyphenyl)sulfanyl]-7-phenylheptanamide

【CA登记号】

【 分 子 式 】C20H25NO3S

【 分 子 量 】359.48944

【元素组成】C 66.82% H 7.01% N 3.9% O 13.35% S 8.92%

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:(VIII)

Horner-Emmons condensation of 5-phenylpentanal (I) with phosphonate (II) in the presence of NaH yielded tert-butyl 7-phenyl-2-heptenoate (III). Subsequent Michael addition of 4-methoxythiophenol (IV) to (III) using a catalytic amount of BuLi provided thioether (V). After acid deprotection of the tert-butyl ester of (V) with TFA, the resulting carboxylic acid (VI) was converted to acid chloride (VII) and then condensed with O-(trimethylsilyl)hydroxylamine to produce hydroxamic acid (VIII). Finally, sulfide oxidation of (VIII) with Oxone furnished the target beta-sulfonylhydroxamic acid. Alternatively tet-butyl ester (III) can be hydrolyzed first to the free acid (IX) with TFA, and then condensed with thiophenol (IV) by means of piperidine to afford the previously described carboxylic acid (VI).

1 Burns, C.J.; Groneberg, R.D.; Morrissette, M.M.; et al.; Dual inhibition of phosphodiesterase 4 and matrix metalloproteinases by an (arylsulfonyl)hydroxamic acid template. J Med Chem 1999, 42, 4, 541.
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
26091 O-(trimethylsilyl)hydroxylamine; (aminooxy)(trimethyl)silane 22737-36-6 C3H11NOSi 详情 详情
(I) 25636 5-phenylpentanal C11H14O 详情 详情
(II) 25637 tert-butyl 2-(diethoxyphosphoryl)acetate 6273-47-8 C10H21O5P 详情 详情
(III) 25638 tert-butyl (E)-7-phenyl-2-heptenoate C17H24O2 详情 详情
(IV) 25639 4-methoxyphenylhydrosulfide; 4-methoxybenzenethiol 34320-82-6 C7H8OS 详情 详情
(V) 25640 tert-butyl 3-[(4-methoxyphenyl)sulfanyl]-7-phenylheptanoate C24H32O3S 详情 详情
(VI) 25641 3-[(4-methoxyphenyl)sulfanyl]-7-phenylheptanoic acid C20H24O3S 详情 详情
(VII) 25642 3-[(4-methoxyphenyl)sulfanyl]-7-phenylheptanoyl chloride C20H23ClO2S 详情 详情
(VIII) 25643 N-hydroxy-3-[(4-methoxyphenyl)sulfanyl]-7-phenylheptanamide C20H25NO3S 详情 详情
(IX) 25644 (E)-7-phenyl-2-heptenoic acid C13H16O2 详情 详情
Extended Information