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【结 构 式】

【分子编号】37267

【品名】methyl (2S)-2-[[(2'-cyano[1,1'-biphenyl]-4-yl)methyl]amino]-3-methylbutanoate

【CA登记号】

【 分 子 式 】C20H22N2O2

【 分 子 量 】322.40696

【元素组成】C 74.51% H 6.88% N 8.69% O 9.92%

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:(V)

This compound has been obtained by two related ways: 1) The hydrolysis of 4'-(bromomethyl)biphenyl-2-carbonitrile (I) with NaOAc in refluxing acetic acid gives the corresponding carbinol (II), which is oxidized with oxalyl chloride in DMSO/dichloromethane yielding the aldehyde (III). The reductocondensation of (III) with L-valine methyl ester (IV) by means of NaBH4CN in THF affords the N-alkylated valine (V), which is acylated with pentanoyl chloride (VI) and TEA in dichloromethane providing the pentanamide (VII). The reaction of the CN group of (VII) with tributyltin azide in refluxing xylene gives the tetrazol derivative (VIII). Finally, the ester group of (VIII) is hydrolyzed with NaOH to furnish the target compound. 2) L-valine methyl ester (IV) can be condensed directly with the bromo-methyl derivative (I) by means of DIEA in dichloromethane giving the N-alkylated valine (V) already reported.

1 Buhlmayer, P.; Ostermayer, F.; Schmidlin, T. (Novartis AG); Acyl cpds.. EP 0443983; JP 1992235149; US 5399578; US 5965592 .
2 Buhlmayer, P.; et al.; Valsartan, a potent, orally active angiotensin II antagonist developed from the structurally new amino acid series. Bioorg Med Chem Lett 1994, 4, 1, 29.
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) 15332 4'-(bromomethyl)[1,1'-biphenyl]-2-carbonitrile; 4'-bromomethyl-2-cyanobiphenyl 114772-54-2 C14H10BrN 详情 详情
(II) 37265 4'-(hydroxymethyl)[1,1'-biphenyl]-2-carbonitrile C14H11NO 详情 详情
(III) 37266 4'-formyl[1,1'-biphenyl]-2-carbonitrile C14H9NO 详情 详情
(IV) 16613 methyl (2S)-2-amino-3-methylbutanoate C6H13NO2 详情 详情
(V) 37267 methyl (2S)-2-[[(2'-cyano[1,1'-biphenyl]-4-yl)methyl]amino]-3-methylbutanoate C20H22N2O2 详情 详情
(VI) 15116 pentanoyl chloride; valeryl chloride 638-29-9 C5H9ClO 详情 详情
(VII) 37268 methyl (2S)-2-[[(2'-cyano[1,1'-biphenyl]-4-yl)methyl](pentanoyl)amino]-3-methylbutanoate C25H30N2O3 详情 详情
(VIII) 37269 methyl (2S)-3-methyl-2-(pentanoyl[[2'-(1H-1,2,3,4-tetraazol-5-yl)[1,1'-biphenyl]-4-yl]methyl]amino)butanoate C25H31N5O3 详情 详情
Extended Information