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【结 构 式】

【分子编号】38461

【品名】methyl (2R,3R)-2-(3-cyanobenzyl)-3-[[(3',4'-dimethoxy[1,1'-biphenyl]-4-yl)carbonyl]amino]butanoate

【CA登记号】

【 分 子 式 】C28H28N2O5

【 分 子 量 】472.5408

【元素组成】C 71.17% H 5.97% N 5.93% O 16.93%

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:(XII)

Protection of methyl (R)-3-aminobutyrate (VI) with di-tert-butyl dicarbonate provided the Boc derivative (VII), which was alkylated with 3-cyanobenzyl bromide (VIII) in the presence of lithium bis(trimethylsilyl)amide at -78 C to afford adduct (IX). Acid deprotection of the Boc group of (IX) yielded amino ester (X). Alternatively, (X) was obtained by protection of methyl 3-aminobutyrate (VI) with benzyl chloroformate, followed by alkylation with 3-cyanobenzyl bromide to give (XI). The carbobenzoxy group of (XI) was then deprotected by hydrogenation over Pd/C. Coupling of amino ester (X) with acid chloride (V) gave rise to amide (XII). Conversion of (XII) to the required amidine was then achieved by treatment with methanolic HCl, followed by reaction of the resulting imidate with ammonia in boiling MeOH. The title compound was isolated after conversion to the trifluoroacetate salt.

1 Gong, Y.; Guertin, K.R.; McGarry, D.G.; Pauls, H.W.; Klein, S.I.; Spada, A.P. (Aventis Pharmaceuticals, Inc.); Substd. N-[(aminoiminomethyl or aminomethyl)phenyl]propyl amides. CA 2264556; EP 0931060; WO 9900356 .
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
10101 Benzyloxycarbonyl chloride; Benzyl chloroformate; 1-[[(Chlorocarbonyl)oxy]methyl]benzene 501-53-1 C8H7ClO2 详情 详情
(V) 38455 3',4'-dimethoxy[1,1'-biphenyl]-4-carbonyl chloride C15H13ClO3 详情 详情
(VI) 38456 methyl (3R)-3-aminobutanoate C5H11NO2 详情 详情
(VII) 38457 methyl (3R)-3-[(tert-butoxycarbonyl)amino]butanoate C10H19NO4 详情 详情
(VIII) 13244 alpha-Bromo-m-tolunitrile; 3-(Bromomethyl)benzonitrile 28188-41-2 C8H6BrN 详情 详情
(IX) 38458 methyl (2R,3R)-3-[(tert-butoxycarbonyl)amino]-2-(3-cyanobenzyl)butanoate C18H24N2O4 详情 详情
(X) 38459 methyl (2R,3R)-3-amino-2-(3-cyanobenzyl)butanoate C13H16N2O2 详情 详情
(XI) 38460 methyl (2R,3R)-3-[[(benzyloxy)carbonyl]amino]-2-(3-cyanobenzyl)butanoate C21H22N2O4 详情 详情
(XII) 38461 methyl (2R,3R)-2-(3-cyanobenzyl)-3-[[(3',4'-dimethoxy[1,1'-biphenyl]-4-yl)carbonyl]amino]butanoate C28H28N2O5 详情 详情
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