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【结 构 式】

【分子编号】33117

【品名】(2S)-2-[((2S)-2-[[(9H-fluoren-9-ylmethoxy)carbonyl]amino]-4-methylpentanoyl)amino]-3-methylbutyric acid

【CA登记号】

【 分 子 式 】C26H32N2O5

【 分 子 量 】452.55056

【元素组成】C 69.01% H 7.13% N 6.19% O 17.68%

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:(IV)

The title compound was obtained by the solid-phase method using a peptide synthesizer. Starting from Fmoc-valine linked to Wang resin (I), cleavage of the Fmoc group with piperidine in DMF provided the deprotected valine-resin (II), which was then coupled with Fmoc-leucine (III) by means of 1-hydroxybenzotriazole and diisopropylcarbodiimide. The resulting dipeptide resin (IV) was deprotected with piperidine in DMF to give (V), and further coupling with protected serine (VI) yielded (VII). After Fmoc-deprotection, the tripeptide-resin (VIII) was coupled with phenyl isocyanate (IX), affording urea (X). Cleavage from the resin with simultaneous deprotection using trifluoroacetic acid furnished the tripeptide urea (XI). This was finally esterified by treatment with ethanolic HCl to provide the target ethyl ester.

1 Sawa, E.; et al.; Structural modification of Fas C-terminal tripeptide and its effects on the inhibitory activity of Fas/FAP-1 binding. J Med Chem 1999, 42, 17, 3289.
2 Kataoka, S.; Nishitoba, T.; Takahashi, M.; Sawa, E.; Kamishohara, M. (Kirin Brewery Co., Ltd.); Novel peptide cpds. and medicinal compsns. thereof. JP 1999171896; WO 9711091 .
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) 19932 (2S)-2-[[(9H-fluoren-9-ylmethoxy)carbonyl]amino]-3-methylbutyric acid C20H21NO4 详情 详情
(II) 21056 (R)-(-)-Valine; D-Valine; (R)-alpha-Aminoisovaleric acid 640-68-6 C5H11NO2 详情 详情
(III) 19934 (2S)-2-[[(9H-fluoren-9-ylmethoxy)carbonyl]amino]-4-methylpentanoic acid C21H23NO4 详情 详情
(IV) 33117 (2S)-2-[((2S)-2-[[(9H-fluoren-9-ylmethoxy)carbonyl]amino]-4-methylpentanoyl)amino]-3-methylbutyric acid C26H32N2O5 详情 详情
(V) 33123 (2S)-2-[[(2S)-2-amino-4-methylpentanoyl]amino]-3-methylbutyric acid 35436-83-0 C11H22N2O3 详情 详情
(VI) 33118 (2S)-3-(tert-butoxy)-2-[[(9H-fluoren-9-ylmethoxy)carbonyl]amino]propionic acid 71989-33-8 C22H25NO5 详情 详情
(VII) 33119 (5S,8S,11S)-5-(tert-butoxymethyl)-1-(9H-fluoren-9-yl)-8-isobutyl-11-isopropyl-3,6,9-trioxo-2-oxa-4,7,10-triazadodecan-12-oic acid C33H45N3O7 详情 详情
(VIII) 33120 (2S)-2-[((2S)-2-[[(2S)-2-amino-3-(tert-butoxy)propanoyl]amino]-4-methylpentanoyl)amino]-3-methylbutyric acid C18H35N3O5 详情 详情
(IX) 11289 1-Isocyanatobenzene; phenyl isocyanate; Phenylisocyanate 103-71-9 C7H5NO 详情 详情
(X) 33121 (2S)-2-[((2S)-2-[[(2S)-2-[(anilinocarbonyl)amino]-3-(tert-butoxy)propanoyl]amino]-4-methylpentanoyl)amino]-3-methylbutyric acid C25H40N4O6 详情 详情
(XI) 33122 (2S)-2-[[(2S)-2-([(2S)-2-[(anilinocarbonyl)amino]-3-hydroxypropanoyl]amino)-4-methylpentanoyl]amino]-3-methylbutyric acid C21H32N4O6 详情 详情
Extended Information