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【结 构 式】

【分子编号】22656

【品名】1-[2-(aminocarbonyl)-1-pyrrolidinyl]-4-methyl-1-oxo-2-pentanaminium chloride

【CA登记号】

【 分 子 式 】C11H22ClN3O2

【 分 子 量 】263.7674

【元素组成】C 50.09% H 8.41% Cl 13.44% N 15.93% O 12.13%

与该中间体有关的原料药合成路线共 2 条

合成路线1

该中间体在本合成路线中的序号:(IV)

a) N-Protected L-Leucine activated as the pentafluorophenyl ester (I) is coupled with L-prolinamide (II), and the resulting dipeptide (III) is deprotected te (IV) and coupled with L-pyro-2-aminoadipic acid pentatluorophenyl ester (V) to give RGH-2202.

1 Kisfaludy, L.; Szporny, L.; Pálosi, É.; Szirtes, T.; Synthesis of thyrotropin-releasing hormone analogu. J Med Chem 1986, 29, 1654.
2 Szirtes, T.; Szporny, L.; Pálosi, É.; Kisfaludy, L.; Synthesis of thyrotropin releasing hormone analogu. J Med Chem 1984, 27, 741.
3 Nogradi, M.; RGH-2202. Drugs Fut 1988, 13, 5, 420.
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) 22653 2,3,4,5,6-pentafluorophenyl 2-[[(benzyloxy)carbonyl]amino]-4-methylpentanoate C20H18F5NO4 详情 详情
(II) 22654 2-pyrrolidinecarboxamide 2812-47-7 C5H10N2O 详情 详情
(III) 22655 benzyl 1-[[2-(aminocarbonyl)-1-pyrrolidinyl]carbonyl]-3-methylbutylcarbamate C19H27N3O4 详情 详情
(IV) 22656 1-[2-(aminocarbonyl)-1-pyrrolidinyl]-4-methyl-1-oxo-2-pentanaminium chloride C11H22ClN3O2 详情 详情
(V) 22657 2,3,4,5,6-pentafluorophenyl (2S)-6-oxo-2-piperidinecarboxylate C12H8F5NO3 详情 详情

合成路线2

该中间体在本合成路线中的序号:(V)

b) Large scale preparation of L-pyro-2-aminoadipic acid (IX) is accomplished by oxidation of the N-protected L-lysine derivative (VI) with KMnO4 followed by deprotection to (VIII) and cyclization.

1 Szirtes, T.; Szporny, L.; Pálosi, É.; Kisfaludy, L.; Synthesis of thyrotropin releasing hormone analogu. J Med Chem 1984, 27, 741.
2 Kisfaludy, L.; Szporny, L.; Pálosi, É.; Szirtes, T.; Synthesis of thyrotropin-releasing hormone analogu. J Med Chem 1986, 29, 1654.
3 Nogradi, M.; RGH-2202. Drugs Fut 1988, 13, 5, 420.
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(A) 22662 2,3,4,5,6-pentafluorophenol 771-61-9 C6HF5O 详情 详情
(V) 22656 1-[2-(aminocarbonyl)-1-pyrrolidinyl]-4-methyl-1-oxo-2-pentanaminium chloride C11H22ClN3O2 详情 详情
(VI) 22658 N(6)-[(benzyloxy)carbonyl]lysine C14H20N2O4 详情 详情
(VII) 22659 N(6)-[(benzyloxy)carbonyl]-6-oxolysine C14H18N2O5 详情 详情
(VIII) 22660 2-aminohexanedioic acid C6H11NO4 详情 详情
(IX) 22661 (2S)-6-oxo-2-piperidinecarboxylic acid C6H9NO3 详情 详情
Extended Information