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【结 构 式】

【分子编号】41852

【品名】2-pyridinylmethyl 2-([[(1S,3S,4S)-4-amino-1-benzyl-3-hydroxy-5-phenylpentyl]amino]carbonyl)phenylcarbamate

【CA登记号】

【 分 子 式 】C32H34N4O4

【 分 子 量 】538.64652

【元素组成】C 71.36% H 6.36% N 10.4% O 11.88%

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:(VII)

The reaction of L-phenylalanine (I) with benzyl chloride and K2CO3 gives the tribenzylated compound (II), which is condensed with acetonitrile by means of NaNH2 yielding 4(S)-(dibenzylamino)-3-oxo-4-phenylbutyronitrile (III). The reaction of (III) with benzylmagnesium chloride in THF affords the unsaturated, partially protected diaminohexenone (IV), which is reduced with NaBH4 and NaBH3(OTf) to provide a mixture of diastereomeric diaminohexanones, from which the desired diastereomer (V) is isolated by crystallization. The acylation of the free amino group of (V) with acylated anthranilic acid (VI) by means of HOBT gives the expected amide (VII), which is debenzylated by treatment with Pd/C and ammonium formate yielding intermediate (VIII). Finally this compound is acylated with the activated N-succinylcarbamate (IX) to afford the desired target compound.

1 Stuk, T.L.; et al.; An efficient stereocontrolled strategy for the synthesis of hydroxyethylene dipeptide isosteres. J Org Chem 1994, 59, 15, 4040.
2 Randad, R.S.; Lubkowska, L.; Eissenstat, M.A.; Gulnik, S.V.; Yu, B.; Bhat, T.N.; Clanton, D.J.; House, T.; Stinson, S.F.; Erickson, J.W.; Unsymmetric nonpeptidic HIV protease inhibitors containing anthranilamide as a P2' ligand. Bioorg Med Chem Lett 1998, 8, 24, 3537.
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) 13952 (S)-(-)-Phenylalanine; L-Phenylalanine 63-91-2 C9H11NO2 详情 详情
(II) 37670 benzyl (2S)-2-(dibenzylamino)-3-phenylpropanoate C30H29NO2 详情 详情
(III) 38263 (4S)-4-(dibenzylamino)-3-oxo-5-phenylpentanenitrile C25H24N2O 详情 详情
(IV) 37671 (2S,4E)-5-amino-2-(dibenzylamino)-1,6-diphenyl-4-hexen-3-one C32H32N2O 详情 详情
(V) 37672 (2S,3S,5S)-5-amino-2-(dibenzylamino)-1,6-diphenyl-3-hexanol C32H36N2O 详情 详情
(V) 41850 2-[[(2-pyridinylmethoxy)carbonyl]amino]benzoic acid C14H12N2O4 详情 详情
(VI) 41851 2-pyridinylmethyl 2-([[(1S,3S,4S)-1-benzyl-4-(dibenzylamino)-3-hydroxy-5-phenylpentyl]amino]carbonyl)phenylcarbamate C46H46N4O4 详情 详情
(VII) 41852 2-pyridinylmethyl 2-([[(1S,3S,4S)-4-amino-1-benzyl-3-hydroxy-5-phenylpentyl]amino]carbonyl)phenylcarbamate C32H34N4O4 详情 详情
(VIII) 41853 1,3-thiazol-5-ylmethyl 2,5-dioxo-1-pyrrolidinecarboxylate C9H8N2O4S 详情 详情
Extended Information