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【结 构 式】 
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【分子编号】59701 【品名】Ethyl (E)-3-(3-fluorophenyl)-2-propenoate; Ethyl 3-fluorocinnamate 【CA登记号】 |
【 分 子 式 】C11H11FO2 【 分 子 量 】194.2055432 【元素组成】C 68.03% H 5.71% F 9.78% O 16.48% |
合成路线1
该中间体在本合成路线中的序号：(III)Ethyl 3-fluorocinnamate (III) was prepared by Wittig condensation of 3-fluorobenzaldehyde (I) with phosphorane (II). Conjugate addition of (R)-N-benzyl-alpha-methylbenzylamine (IV) to the unsaturated ester (III) furnished the chiral amino ester (V). The primary amine (VI) was then obtained by hydrogenolysis of the N-benzyl groups in the presence of palladium hydroxyde. Coupling of the known pyrrolidinoneacetic acid (VII) to the amino ester (VI) by means of EDC/HOBt afforded amide (VIII). Finally, saponification of the ethyl ester group of (VIII) led to the corresponding carboxylic acid.
| 【1】 Brashear, K.M.; Hunt, C.A.; Coleman, P.J.; et al.; Non-peptide alphavbeta3 antagonists. Part 3: Identification of potent RGD mimetics incorporating novel beta-amino acids as aspartic acid replacements. Bioorg Med Chem Lett 2002, 12, 1, 31. |
| 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) | 18887 | 3-Fluorobenzaldehyde | 456-48-4 | C7H5FO | 详情 | 详情 |
| (II) | 14182 | ethyl 2-(triphenyl-lambda(5)-phosphanylidene)acetate; (Carbethoxymethylene)triphenylphosphorane | 1099-45-2 | C22H21O2P | 详情 | 详情 |
| (III) | 59701 | Ethyl (E)-3-(3-fluorophenyl)-2-propenoate; Ethyl 3-fluorocinnamate | C11H11FO2 | 详情 | 详情 | |
| (IV) | 47881 | (1R)-N-benzyl-1-phenyl-1-ethanamine; N-benzyl-N-[(1R)-1-phenylethyl]amine | C15H17N | 详情 | 详情 | |
| (V) | 59702 | ethyl (3S)-3-{benzyl[(1R)-1-phenylethyl]amino}-3-(3-fluorophenyl)propanoate | C26H28FNO2 | 详情 | 详情 | |
| (VI) | 59703 | ethyl (3S)-3-amino-3-(3-fluorophenyl)propanoate | C11H14FNO2 | 详情 | 详情 | |
| (VII) | 59704 | 2-{(3S)-2-oxo-3-[2-(5,6,7,8-tetrahydro[1,8]naphthyridin-2-yl)ethyl]pyrrolidinyl}acetic acid | C16H21N3O3 | 详情 | 详情 | |
| (VIII) | 59705 | ethyl (3S)-3-(3-fluorophenyl)-3-[(2-{(3S)-2-oxo-3-[2-(5,6,7,8-tetrahydro[1,8]naphthyridin-2-yl)ethyl]pyrrolidinyl}acetyl)amino]propanoate | C27H33FN4O4 | 详情 | 详情 |