L-756423, -Drug Synthesis Database

【结构式】

【药物名称】L-756423

【化学名称】4-(2-Benzo[b]furanyl)-N-tert-butyl-1-[2(S)-hydroxy-4(R)-[N-[2(R)-hydroxyindan-1(S)-yl]carbamoyl]-5-phenylpentyl]piperazine-2(S)-carboxamide
　　　　　　2(R)-Benzyl-5-[4-(2-benzo[b]furanyl)-2(S)-(N-tert-butylcarbamoyl)piperazin-1-yl]-4(S)-hydroxy-N-[2(R)-hydroxyindan-1(S)-yl]pentanamide

【CA登记号】216863-66-0

【分子式】C₃₉H₄₈N₄O₅

【分子量】652.84121

【开发单位】Merck & Co. (Originator)

【药理作用】AIDS Medicines, Anti-HIV Agents, ANTIINFECTIVE THERAPY, HIV Protease Inhibitors

合成路线1

Compound (I) (intermediate no. (VIII) in scheme no. 19918301a) is a key intermediate in the synthesis of indinavir. For the synthesis of the product 285239, (I) is coupled with benzofuran-2-carbaldehyde (II) via a reductive amination by means of NaBH(OAc)3 either in 1,2-dichloroethane/AcOH or in isopropyl acetate/AcOH.

参考文献中间体

【1】 McDaniel, S.L.; McDonough, C.; Dorsey, B.D.; et al.; Identification of MK-944a: A second clinical candidate from the hydroxylaminepentanamide isostere series of HIV protease inhibitors. J Med Chem 2000, 43, 18, 3386.
【3】 Lin, J.H.; Chodakewitz, J.A.; Deutsch, P.J.; Vacca, J.P.; Yeh, K.C.; Ju, W.D. (Merck & Co., Inc.); Combination therapy for the treatment of AIDS. WO 9925352 .
【2】 Hoerrner, R.S.; Volante, R.P.; Purick, R.M.; Askin, D.; Reider, P.; Varsolona, R.J. (Merck & Co., Inc.); Sulfate salt of an HIV protease inhibitor having an improved oral absorption and bioavailability. EP 0986554; JP 2000513747; US 6071916; WO 9854178 .

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)	16245	(2S)-1-((2S,4R)-4-benzyl-2-hydroxy-5-[[(1S,2R)-2-hydroxy-2,3-dihydro-1H-inden-1-yl]amino]-5-oxopentyl)-N-(tert-butyl)-2-piperazinecarboxamide		C₃₀H₄₂N₄O₄	详情	详情
(II)	45443	Benzofuran-2-carbaldehyde; 1-benzofuran-2-carbaldehyde	4265-16-1	C₉H₆O₂	详情	详情

Extended Information