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【结 构 式】

【分子编号】19035

【品名】(2R)-2-[[(9H-fluoren-9-ylmethoxy)carbonyl]amino]-5-[(imino[[(2,2,5,7,8-pentamethyl-3,4-dihydro-2H-chromen-6-yl)sulfonyl]amino]methyl)amino]pentanoic acid

【CA登记号】119831-72-0

【 分 子 式 】C35H42N4O7S

【 分 子 量 】662.80724

【元素组成】C 63.42% H 6.39% N 8.45% O 16.9% S 4.84%

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:(VI)

Fmoc-protected phenylalanine (I) is attached to Rink resin by means of DCC and HOBt coupling, to give the amino acid-resin complex (II). Then, N-Fmoc protecting group is removed with piperidine in DMF to afford (III). This is submitted to further sequential amino acid coupling and deprotection cycles with Fmoc-phenylalanine (I) and alpha-Fmoc-omega-pmc-D-arginine (VI) to yield in turn resins (V) and (VII), respectively.

1 Brown, W.; DiMaio, J.; Schiller, P.; Martel, R. (AstraZeneca plc); Novel opioid peptides for the treatment of pain and use thereof. JP 1997509168; WO 9522557 .
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) 19030 (2S)-2-[[(9H-fluoren-9-ylmethoxy)carbonyl]amino]-3-phenylpropionic acid; N-((9H-fluoren-9-ylmethoxy)carbonyl)-phenylalanine 35661-40-6 C24H21NO4 详情 详情
(II) 19031 9H-fluoren-9-ylmethyl (1S)-2-amino-1-benzyl-2-oxoethylcarbamate C24H22N2O3 详情 详情
(III) 19032 (2S)-2-amino-3-phenylpropanamide 5241-58-7 C9H12N2O 详情 详情
(IV) 19033 9H-fluoren-9-ylmethyl (1S)-2-[[(1S)-2-amino-1-benzyl-2-oxoethyl]amino]-1-benzyl-2-oxoethylcarbamate C33H31N3O4 详情 详情
(V) 19034 (2S)-2-amino-N-[(1S)-2-amino-1-benzyl-2-oxoethyl]-3-phenylpropanamide C18H21N3O2 详情 详情
(VI) 19035 (2R)-2-[[(9H-fluoren-9-ylmethoxy)carbonyl]amino]-5-[(imino[[(2,2,5,7,8-pentamethyl-3,4-dihydro-2H-chromen-6-yl)sulfonyl]amino]methyl)amino]pentanoic acid 119831-72-0 C35H42N4O7S 详情 详情
(VII) 19036 9H-fluoren-9-ylmethyl (1R)-1-[[((1S)-2-[[(1S)-2-amino-1-benzyl-2-oxoethyl]amino]-1-benzyl-2-oxoethyl)amino]carbonyl]-4-[(imino[[(2,2,5,7,8-pentamethyl-3,4,4a,8a-tetrahydro-2H-chromen-6-yl)sulfonyl]amino]methyl)amino]butylcarbamate C53H63N7O8S 详情 详情

合成路线2

该中间体在本合成路线中的序号:(III)

The title compound was prepared by solid-phase peptide synthesis starting from N-Fmoc-D-proline linked to Rink resin (I). Deprotection of the Fmoc group by means of piperidine in DMA afforded proline-resin (II). Coupling of N-alpha-Fmoc-NG-Pmc-D-arginine (III) to proline-resin (II) using diisopropyl carbodiimide (DIC) and HOBt, followed by Fmoc deprotection with piperidine in DMA, furnished dipeptide-resin (IV). Further coupling and deprotection cycles incorporating the amino acid N2-Fmoc-N6-Boc-D-lysine (V) (twice) and the peptoid residue N-Fmoc-N-[3-(3-Pmc-guanidino)propyl]glycine (VIII) yielded the peptide resins (VI), (VII) and (IX), respectively.

1 Hamy, F.; et al.; An inhibitor of the Tat/TAR RNA interaction that effectively suppresses HIV-1 replication. Proceedings of the National Academy of Sciences of the United States of America 1997, 94, 8, 3548.
2 Felder, E.; Hamy, F.; Heizmann, G.; Klimkait, T.; Lazdins, J.K. (Novartis AG); Antiviral peptoid cpds.. EP 0832110; WO 9640759 .
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) 42841 9H-fluoren-9-ylmethyl (2R)-2-(aminocarbonyl)-1-pyrrolidinecarboxylate C20H20N2O3 详情 详情
(II) 37077 (2R)-2-pyrrolidinecarboxamide C5H10N2O 详情 详情
(III) 19035 (2R)-2-[[(9H-fluoren-9-ylmethoxy)carbonyl]amino]-5-[(imino[[(2,2,5,7,8-pentamethyl-3,4-dihydro-2H-chromen-6-yl)sulfonyl]amino]methyl)amino]pentanoic acid 119831-72-0 C35H42N4O7S 详情 详情
(IV) 42842 (2R)-1-[(2R)-2-amino-5-[(imino[[(2,2,5,7,8-pentamethyl-3,4,4a,8a-tetrahydro-2H-chromen-6-yl)sulfonyl]amino]methyl)amino]pentanoyl]-2-pyrrolidinecarboxamide C25H42N6O5S 详情 详情
(V) 42847 (2R)-6-[(tert-butoxycarbonyl)amino]-2-[[(9H-fluoren-9-ylmethoxy)carbonyl]amino]hexanoic acid C26H32N2O6 详情 详情
(VI) 42843 tert-butyl (5R)-5-amino-6-([(1R)-1-[[(2R)-2-(aminocarbonyl)pyrrolidinyl]carbonyl]-4-[(imino[[(2,2,5,7,8-pentamethyl-3,4,4a,8a-tetrahydro-2H-chromen-6-yl)sulfonyl]amino]methyl)amino]butyl]amino)-6-oxohexylcarbamate C36H62N8O8S 详情 详情
(VII) 42844 tert-butyl (5R)-5-amino-6-([(1R)-1-[([(1R)-1-[[(2R)-2-(aminocarbonyl)pyrrolidinyl]carbonyl]-4-[(imino[[(2,2,5,7,8-pentamethyl-3,4,4a,8a-tetrahydro-2H-chromen-6-yl)sulfonyl]amino]methyl)amino]butyl]amino)carbonyl]-5-[(tert-butoxycarbonyl)amino]pentyl C47H82N10O11S 详情 详情
(VIII) 42845 2-([(9H-fluoren-9-ylmethoxy)carbonyl][3-[(imino[[(2,2,5,7,8-pentamethyl-3,4,4a,8a-tetrahydro-2H-chromen-6-yl)sulfonyl]amino]methyl)amino]propyl]amino)acetic acid C35H44N4O7S 详情 详情
(IX) 42846 tert-butyl (5R,8R)-5-[([(1R)-1-[[(2R)-2-(aminocarbonyl)pyrrolidinyl]carbonyl]-4-[(imino[[(2,2,5,7,8-pentamethyl-3,4,4a,8a-tetrahydro-2H-chromen-6-yl)sulfonyl]amino]methyl)amino]butyl]amino)carbonyl]-8-[4-[(tert-butoxycarbonyl)amino]butyl]-17-imino-7 C67H114N14O15S2 详情 详情
Extended Information