methyl 3-[(2-aminoacetyl)amino]-3-[4-(1-naphthyl)phenyl]propanoate -Drug Synthesis Database

【结构式】

【分子编号】54768

【品名】methyl 3-[(2-aminoacetyl)amino]-3-[4-(1-naphthyl)phenyl]propanoate

【CA登记号】

【分子式】C₂₂H₂₂N₂O₃

【分子量】362.42836

【元素组成】C 72.91% H 6.12% N 7.73% O 13.24%

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：(VI)

The 3-aryl-3-aminopropionic acid (II) was prepared by Knoevenagel condensation of 4-(1-naphthyl)benzaldehyde (I) with malonic acid in the presence of ammonium acetate. Subsequent esterification of (II) by means of thionyl chloride and methanol afforded the methyl ester (III). Coupling of amino ester (III) with N-Boc-glycine (IV) by means of TBTU and HOBt furnished amide (V). After acidic Boc group cleavage, the resultant dipeptide ester (VI) was acylated with 4-(4-methylpyridin-2-ylamino)butyric acid (VII), yielding tripeptide ester (VIII). The methyl ester group of (VIII) was finally hydrolyzed by NaOH in aqueous dioxan.

参考文献中间体

合成目标

【1】 Goodman, S.L.; Holzemann, G.; Kessler, H.; Sulyok, G.A.G.; Nanomolar small molecule inhibitors for alphavbeta6, alphavbeta5, and +alphavbeta3 integrins. J Med Chem 2002, 45, 5, 1045.
【2】 Holzemann, G.; Jonczyk, A.; Goodman, S.; Stahle, W. (Merck Patent GmbH); beta-Alanine derivs.. WO 0048996 .

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)	54764	4-(1-naphthyl)benzaldehyde		C₁₇H₁₂O	详情	详情
(II)	54765	3-[4-(1-naphthyl)phenyl]-beta-alanine		C₁₉H₁₇NO₂	详情	详情
(III)	54766	methyl 3-amino-3-[4-(1-naphthyl)phenyl]propanoate		C₂₀H₁₉NO₂	详情	详情
(IV)	18066	N-alpha-t-BOC-glycine; 2-[(tert-butoxycarbonyl)amino]acetic acid	4530-20-5	C₇H₁₃NO₄	详情	详情
(V)	54767	methyl 3-({2-[(tert-butoxycarbonyl)amino]acetyl}amino)-3-[4-(1-naphthyl)phenyl]propanoate		C₂₇H₃₀N₂O₅	详情	详情
(VI)	54768	methyl 3-[(2-aminoacetyl)amino]-3-[4-(1-naphthyl)phenyl]propanoate		C₂₂H₂₂N₂O₃	详情	详情
(VII)	54769	4-[(4-methyl-2-pyridinyl)amino]butanoic acid		C₁₀H₁₄N₂O₂	详情	详情
(VIII)	54770	methyl 3-{[2-({4-[(4-methyl-2-pyridinyl)amino]butanoyl}amino)acetyl]amino}-3-[4-(1-naphthyl)phenyl]propanoate		C₃₂H₃₄N₄O₄	详情	详情

Extended Information