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【结 构 式】 
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【分子编号】51051 【品名】 【CA登记号】 |
【 分 子 式 】C42H54N10O11S 【 分 子 量 】907.01756 【元素组成】C 55.62% H 6% N 15.44% O 19.4% S 3.54% |
合成路线1
该中间体在本合成路线中的序号：(XI)Coupling of N-Boc-D-pyridylalanine (I) to glycine methyl ester (II) produced the protected dipeptide (III). Subsequent catalytic hydrogenation of the pyridine ring of (III) over PtO2 gave piperidine (IV), which was then treated with the guanylating reagent (V) to afford the guanidine derivative (VI). Acid cleavage of the Boc protecting group of (VI) provided amine (VII). This was condensed with benzylsulfonyl chloride to give sulfonamide (VIII). After basic hydrolysis of the methyl ester of (VIII), the resultant carboxylic acid (IX) was coupled to nitroargininal ethyl aminal (X), yielding amide (XI).
| 【1】 Levy, O.E.; Uong, T.H.; Tamura, S.Y.; et al.; Guanylpiperidine peptidomimetics: Potent and selective bis-cation inhibitors of factor Xa. Bioorg Med Chem Lett 2000, 10, 8, 745. |
| 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) | 51044 | Boc-D-4-Pyridylalanine; Boc-D-4-Pyridylala | 37535-58-3 | C13H18N2O4 | 详情 | 详情 |
| (II) | 17568 | methyl 2-aminoacetate | C3H7NO2 | 详情 | 详情 | |
| (III) | 51045 | methyl 2-[[(2R)-2-[(tert-butoxycarbonyl)amino]-3-(4-pyridinyl)propanoyl]amino]acetate | C16H23N3O5 | 详情 | 详情 | |
| (IV) | 51046 | methyl 2-[[(2R)-2-[(tert-butoxycarbonyl)amino]-3-(4-piperidinyl)propanoyl]amino]acetate | C16H29N3O5 | 详情 | 详情 | |
| (V) | 32861 | benzyl (E)-[[(benzyloxy)carbonyl]amino](methylsulfanyl)methylidenecarbamate | C18H18N2O4S | 详情 | 详情 | |
| (VI) | 51047 | methyl 2-([(2R)-3-[1-([[(benzyloxy)carbonyl]amino][[(benzyloxy)carbonyl]imino]methyl)-4-piperidinyl]-2-[(tert-butoxycarbonyl)amino]propanoyl]amino)acetate | C33H43N5O9 | 详情 | 详情 | |
| (VII) | 51048 | methyl 2-([(2R)-2-amino-3-[1-([[(benzyloxy)carbonyl]amino][[(benzyloxy)carbonyl]imino]methyl)-4-piperidinyl]propanoyl]amino)acetate | C28H35N5O7 | 详情 | 详情 | |
| (VIII) | 51049 | methyl 2-([(2R)-3-[1-([[(benzyloxy)carbonyl]amino][[(benzyloxy)carbonyl]imino]methyl)-4-piperidinyl]-2-[(benzylsulfonyl)amino]propanoyl]amino)acetate | C35H41N5O9S | 详情 | 详情 | |
| (IX) | 51050 | 2-([(2R)-3-[1-([[(benzyloxy)carbonyl]amino][[(benzyloxy)carbonyl]imino]methyl)-4-piperidinyl]-2-[(benzylsulfonyl)amino]propanoyl]amino)acetic acid | C34H39N5O9S | 详情 | 详情 | |
| (X) | 29388 | 3(S)-Amino-2-ethoxy-N2-nitropiperidine-1-carboxamidine | C8H17N5O3 | 详情 | 详情 | |
| (XI) | 51051 | C42H54N10O11S | 详情 | 详情 |
合成路线2
该中间体在本合成路线中的序号：(XI)Hydrogenolysis of the carbobenzoxy and nitro protecting groups of (XI) furnished (XII). Finally, mild acid hydrolysis of the ethyl aminal group of (XII) gave the title compound, which was isolated as the trifluoroacetate salt.
| 【1】 Levy, O.E.; Uong, T.H.; Tamura, S.Y.; et al.; Guanylpiperidine peptidomimetics: Potent and selective bis-cation inhibitors of factor Xa. Bioorg Med Chem Lett 2000, 10, 8, 745. |