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【结 构 式】 
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【分子编号】37251 【品名】(2R)-2-[[(benzyloxy)carbonyl]amino]-4-[(tert-butoxycarbonyl)amino]butyric acid 【CA登记号】 |
【 分 子 式 】C17H24N2O6 【 分 子 量 】352.38744 【元素组成】C 57.94% H 6.86% N 7.95% O 27.24% |
合成路线1
该中间体在本合成路线中的序号：(II)Nalpha-(Benzyloxycarbonyl)-1,4-diaminobutyric acid (I) was protected as the Nomega-Boc derivative (II) and then coupled to glycine ethyl ester (III) by means of EDC and HOBt to produce dipeptide (IV). Hydrogenolysis of the benzyloxycarbonyl group of (IV) to give (V), followed by condensation with alpha-toluenesulfonyl chloride (VI) gave sulfonamide (VII). Side-chain deprotection of (VII) with HCl liberated amine (VIII), which was acylated with 2-pyrazinecarboxylic acid (IX) to afford amide (X). Saponification of the ethyl ester of (X) with LiOH gave carboxylic acid (XI).
| 【1】 Ho, J.Z.; et al.; Exploration solid-phase synthesis of factor Xa inhibitors: Discovery and application of P3-heterocyclic amides as novel types of non-basic arginine surrogates. Bioorg Med Chem Lett 1999, 9, 24, 3459. |
| 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) | 37250 | (2R)-4-amino-2-[[(benzyloxy)carbonyl]amino]butyric acid | 62234-40-6 | C12H16N2O4 | 详情 | 详情 |
| (II) | 37251 | (2R)-2-[[(benzyloxy)carbonyl]amino]-4-[(tert-butoxycarbonyl)amino]butyric acid | C17H24N2O6 | 详情 | 详情 | |
| (III) | 10309 | ethyl 2-aminoacetate; Glycine ethyl ester | 459-73-4 | C4H9NO2 | 详情 | 详情 |
| (IV) | 37252 | ethyl 2-([(2R)-2-[[(benzyloxy)carbonyl]amino]-4-[(tert-butoxycarbonyl)amino]butanoyl]amino)acetate | C21H31N3O7 | 详情 | 详情 | |
| (V) | 37253 | ethyl 2-([(2R)-2-amino-4-[(tert-butoxycarbonyl)amino]butanoyl]amino)acetate | C13H25N3O5 | 详情 | 详情 | |
| (VI) | 25151 | phenylmethanesulfonyl chloride | 1939-99-7 | C7H7ClO2S | 详情 | 详情 |
| (VII) | 37254 | ethyl 2-([(2R)-2-[(benzylsulfonyl)amino]-4-[(tert-butoxycarbonyl)amino]butanoyl]amino)acetate | C20H31N3O7S | 详情 | 详情 | |
| (VIII) | 37255 | ethyl 2-([(2R)-4-amino-2-[(benzylsulfonyl)amino]butanoyl]amino)acetate | C15H23N3O5S | 详情 | 详情 | |
| (IX) | 37256 | 2-pyrazinecarboxylic acid; Pyrazinoic acid | 98-97-5 | C5H4N2O2 | 详情 | 详情 |
| (X) | 37257 | ethyl 2-([(2R)-2-[(benzylsulfonyl)amino]-4-[(2-pyrazinylcarbonyl)amino]butanoyl]amino)acetate | C20H25N5O6S | 详情 | 详情 | |
| (XI) | 37258 | 2-([(2R)-2-[(benzylsulfonyl)amino]-4-[(2-pyrazinylcarbonyl)amino]butanoyl]amino)acetic acid | C18H21N5O6S | 详情 | 详情 |