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【结 构 式】

【分子编号】43542

【品名】benzyl (E)-amino[(3S)-3-amino-2-oxopiperidinyl]methylidenecarbamate

【CA登记号】

【 分 子 式 】C14H18N4O3

【 分 子 量 】290.32208

【元素组成】C 57.92% H 6.25% N 19.3% O 16.53%

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:(XI)

Solution-phase synthesis: Protection of the side-chain of Boc-Arg-OH (IX) by treatment with Cbz-Cl in aqueous NaHCO3 yields Boc-Arg(Cbz)-OH (X), which is then converted into arginine lactam (XI) by a first treatment with isobutyl chloroformate (i-BuO2CCl) and NMM in THF followed by Boc deprotection with HCl/dioxane. Condensation of N-deprotected lactam (XI) with protected dipeptide (XII) by means of BOP/DIEA in DMF provides the tripeptide lactam (XIII), which is finally reduced with LiAlH4 in THF and hydrogenated over Pd/C for protecting group removal.

1 Marlowe, C.K.; Sinha, U.; Scarborough, R.M.; Gunn, A.C.; Design, synthesis and structure-activity relationship of a series of arginine aldehyde factor Xa inhibitors. Part 1: Structures based on the (D)-Arg-Gly-Arg tripeptide sequence. Bioorg Med Chem Lett 2000, 10, 1, 13.
2 Marlowe, C.K.; Scarborough, R.M.; Laibelman, A.M.; Sinha, U.; Zhu, B.-Y. (COR Therapeutics, Inc.); Inhibitors of factor Xa. EP 0846125; JP 1999507626; US 5919765; WO 9640743 .
3 Marlowe, C.K.; Scarborough, R.M.; Laibelman, A.M.; Sinha, U.; Zhu, B.-Y. (COR Therapeutics, Inc.); Inhibitors of factor Xa. US 5721214 .
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(IX) 14073 (2S)-5-[[Amino(imino)methyl]amino]-2-[(tert-butoxycarbonyl)amino]pentanoic acid 13726-76-6 C11H22N4O4 详情 详情
(X) 14074 (2S)-5-[(Amino[[(benzyloxy)carbonyl]imino]methyl)amino]-2-[(tert-butoxycarbonyl)amino]pentanoic acid C19H28N4O6 详情 详情
(XI) 43542 benzyl (E)-amino[(3S)-3-amino-2-oxopiperidinyl]methylidenecarbamate C14H18N4O3 详情 详情
(XII) 43543 (E,10R)-5-amino-10-[(benzylsulfonyl)amino]-3,11-dioxo-1-phenyl-2-oxa-4,6,12-triaza-4-tetradecen-14-oic acid C23H29N5O7S 详情 详情
(XIII) 43544 benzyl (E)-amino([(4R)-5-[(2-[[(3S)-1-(amino[[(benzyloxy)carbonyl]imino]methyl)-2-oxopiperidinyl]amino]-2-oxoethyl)amino]-4-[(benzylsulfonyl)amino]-5-oxopentyl]amino)methylidenecarbamate C37H45N9O9S 详情 详情
Extended Information