• English
  • 简体中文
Login Register
Current Location: Home > Feedback Help Print

【结 构 式】

【分子编号】41937

【品名】benzyl (2S)-2-[[(2'-cyano[1,1'-biphenyl]-4-yl)methyl]amino]-3-methylbutanoate; N-[(2'-cyanobiphenyl-4-yl)methyl]-L-valine benzyl ester

【CA登记号】137864-23-4

【 分 子 式 】C26H26N2O2

【 分 子 量 】398.50472

【元素组成】C 78.36% H 6.58% N 7.03% O 8.03%

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)

The reaction of 2-bromo-4'-methylbiphenyl (I) with 14C labeled cuprous cyanide in refluxing DMF gives 4'-methylbiphenyl-2-carbonitrile (II), which is brominated with NBS and AIBN in refluxing CCl4 to yield the bromomethyl derivative (III). The condensation of (III) with L-valine benzyl ester (IV) by means of DIEA in hot DMF affords the N-substituted valine (V), which is acylated with pentanoyl chloride (VI) and DIEA to provide the N-acylated valine (VII). The cyclization of the cyano group of (VII) with tributyltin azide at 140 C furnishes the tetrazol derivative (VIII) which is finally debenzylated by hydrogenation with H2 over Pd/C in dioxane.

1 Moenius, T.; et al.; Carbon-14 labelling of Diovan(TM) in its valine-moiety. J Label Compd Radiopharm 2000, 43, 13, 1245.
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) 41935 2-bromo-4'-methyl-1,1'-biphenyl C13H11Br 详情 详情
(II) 13929 2-Cyano-4'-methylbiphenyl; 4'-Methyl[1,1'-biphenyl]-2-carbonitrile 114772-53-1 C14H11N 详情 详情
(II) 45264 4'-methyl[1,1'-biphenyl]-2-carbonitrile C14H11N 详情 详情
(III) 15332 4'-(bromomethyl)[1,1'-biphenyl]-2-carbonitrile; 4'-bromomethyl-2-cyanobiphenyl 114772-54-2 C14H10BrN 详情 详情
(III) 45265 4'-(bromomethyl)[1,1'-biphenyl]-2-carbonitrile C14H10BrN 详情 详情
(IV) 41936 benzyl (2S)-2-amino-3-methylbutanoate C12H17NO2 详情 详情
(V) 41937 benzyl (2S)-2-[[(2'-cyano[1,1'-biphenyl]-4-yl)methyl]amino]-3-methylbutanoate; N-[(2'-cyanobiphenyl-4-yl)methyl]-L-valine benzyl ester 137864-23-4 C26H26N2O2 详情 详情
(V) 45266 benzyl (2S)-2-[[(2'-cyano[1,1'-biphenyl]-4-yl)methyl]amino]-3-methylbutanoate C26H26N2O2 详情 详情
(VI) 15116 pentanoyl chloride; valeryl chloride 638-29-9 C5H9ClO 详情 详情
(VII) 41938 benzyl (2S)-2-[[(2'-cyano[1,1'-biphenyl]-4-yl)methyl](pentanoyl)amino]-3-methylbutanoate C31H34N2O3 详情 详情
(VII) 45267 benzyl (2S)-2-[[(2'-cyano[1,1'-biphenyl]-4-yl)methyl](pentanoyl)amino]-3-methylbutanoate C31H34N2O3 详情 详情
(VIII) 41939 benzyl (2S)-3-methyl-2-(pentanoyl[[2'-(1H-1,2,3,4-tetraazol-5-yl)[1,1'-biphenyl]-4-yl]methyl]amino)butanoate C31H35N5O3 详情 详情
(VIII) 45268 benzyl (2S)-3-methyl-2-(pentanoyl[[2'-(1H-1,2,3,4-tetraazol-5-yl)[1,1'-biphenyl]-4-yl]methyl]amino)butanoate C31H35N5O3 详情 详情
Extended Information