ethyl (E)-2-methyl-7-phenyl-2-heptenoate -Drug Synthesis Database

【结构式】

【分子编号】26081

【品名】ethyl (E)-2-methyl-7-phenyl-2-heptenoate

【CA登记号】

【分子式】C₁₆H₂₂O₂

【分子量】246.34948

【元素组成】C 78.01% H 9% O 12.99%

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 reaction of 5-phenylpentanal (I) with triethyl 2-phosphonopropionate (II) by means of NaOEt in THF gives ethyl 2-methyl-7-phenyl-2(E)-heptenoate (III), which is hydrolyzed with NaOH in methanol/water to the corresponding free acid (IV). The reaction of (IV) with 4-methoxythiophenol (V) in hot piperidine affords 3-(4-methoxyphenylsulfanyl)-2-methyl-7-phenylheptanoic acid (VI), which by reaction first with oxalyl chloride, then with O-trimethylsilylhydroxylamine (VII) in dichloromethane, and finally with HCl is converted into the hydroxamic acid (VIII). Finally, this compound is oxidized with oxone in methanol/water to provide the target compound as mixture of diastereomeric racemates that is separated by reversed phase HPLC.

参考文献中间体

合成目标

【1】 Groneberg, R.D.; Neuenschwander, K.W.; Djuric, S.W.; McGeehan, G.M.; Burns, C.J.; Condon, S.M.; Morrissette, M.M.; Salvino, J.M.; Scotese, A.C.; Ullrich, J.W. (Aventis Pharma SA); Substd. (aryl, heteroaryl, arylmethyl or heteroarylmethyl) hydroxamic acid cpds.. EP 0871439; JP 2000503012; WO 9724117 .

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)	25636	5-phenylpentanal		C₁₁H₁₄O	详情	详情
(II)	18816	ethyl 2-(diethoxyphosphoryl)propanoate	3699-66-9	C₉H₁₉O₅P	详情	详情
(III)	26081	ethyl (E)-2-methyl-7-phenyl-2-heptenoate		C₁₆H₂₂O₂	详情	详情
(IV)	26082	(E)-2-methyl-7-phenyl-2-heptenoic acid		C₁₄H₁₈O₂	详情	详情
(V)	25639	4-methoxyphenylhydrosulfide; 4-methoxybenzenethiol	34320-82-6	C₇H₈OS	详情	详情
(VI)	26083	3-[(4-methoxyphenyl)sulfanyl]-2-methyl-7-phenylheptanoic acid		C₂₁H₂₆O₃S	详情	详情
(VII)	26091	O-(trimethylsilyl)hydroxylamine; (aminooxy)(trimethyl)silane	22737-36-6	C₃H₁₁NOSi	详情	详情
(VIII)	26084	N-hydroxy-3-[(4-methoxyphenyl)sulfanyl]-2-methyl-7-phenylheptanamide		C₂₁H₂₇NO₃S	详情	详情

Extended Information