【结 构 式】 |
【分子编号】61411 【品名】methyl (2R)-2-amino-3-(4-pyridinyl)propanoate 【CA登记号】 |
【 分 子 式 】C9H12N2O2 【 分 子 量 】180.20656 【元素组成】C 59.99% H 6.71% N 15.55% O 17.76% |
合成路线1
该中间体在本合成路线中的序号:(II)N-Boc-L-(4-Pyridyl)alanine (I) is deprotected and esterified by means of a methanolic solution of SOCl2 to produce amino ester (II). Subsequent acylation of (II) with benzoyl chloride affords benzamide (III). Ester group reduction in (III) by means of NaBH4 yields alcohol (IV). The amide function of (IV) is then hydrolyzed under acidic conditions to furnish (S)-2-amino-3-(4-pyridyl)-1-propanol (V). Coupling of amino alcohol (V) with the known 6-(methylthio)purine (VI) in hot pyridine leads to adduct (VII). Intramolecular cyclization of the purine alcohol (VII) employing thionyl chloride produces the target tricyclic compound, which is finally isolated as the corresponding D-tartrate salt.
【1】 Ueno, K.; et al.; A new class of antidiabetic drugs; insulin secretion potentiator: Synthesis and biological activity of imidazopurine derivatives. 22nd Symp Med Chem (Nov 27 2002, Shizuoka) 2002, Abst 2P-05. |
【2】 Nomoto, Y.; Nakanishi, S.; Ohta, Y.; Ogawa, A.; Suzuki, C.; Ueno, K.; Yano, H.; Kusaka, H.; Takasaki, K. (Kyowa Hakko Kogyo Co., Ltd.); Fused purine derivs.. EP 1251130; WO 0147931 . |
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) | 61411 | methyl (2R)-2-amino-3-(4-pyridinyl)propanoate | C9H12N2O2 | 详情 | 详情 | |
(III) | 61412 | methyl (2R)-2-(benzoylamino)-3-(4-pyridinyl)propanoate | C16H16N2O3 | 详情 | 详情 | |
(IV) | 61413 | N-[(1R)-2-hydroxy-1-(4-pyridinylmethyl)ethyl]benzamide | C15H16N2O2 | 详情 | 详情 | |
(V) | 61414 | (2R)-2-amino-3-(4-pyridinyl)-1-propanol | C8H12N2O | 详情 | 详情 | |
(VI) | 61415 | 8-cyclopentyl-6-(methylsulfanyl)-3-propyl-3,7-dihydro-2H-purin-2-one | C14H20N4OS | 详情 | 详情 | |
(VII) | 61416 | 8-cyclopentyl-6-{[(1R)-2-hydroxy-1-(4-pyridinylmethyl)ethyl]amino}-3-propyl-3,7-dihydro-2H-purin-2-one | C21H28N6O2 | 详情 | 详情 |