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【结 构 式】

【分子编号】39332

【品名】diethyl 2-[4-[(2S)-2-amino-3-oxo-3-(pentylamino)propyl]phenoxy]malonate

【CA登记号】

【 分 子 式 】C21H32N2O6

【 分 子 量 】408.49496

【元素组成】C 61.75% H 7.9% N 6.86% O 23.5%

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:(VI)

Coupling of N-Cbz-tyrosine (I) with n-pentylamine (II) afforded amide (III). Subsequent alkylation of the phenol group of (III) with diethyl chloromalonate (IV) gave phenoxy malonate (V). Hydrogenolytical deprotection of the N-Cbz group of (V) provided the corresponding amine, which was isolated as the hydrochloride salt (VI). Conversion of (VI) to isocyanate (VII) was effected by treatment with diphosgene in the presence of Proton Sponge(r). Addition of phenylalanine ethyl ester (VIII) to isocyanate (VII) furnished urea (IX). Finally, the ethyl ester groups of (IX) were saponified with LiOH to yield the title compound.

1 Bleasdale, J.; May, P.D.; Schostarez, H.J.; Barf, T.; Larsen, S.D.; Liljebris, C. (Pharmacia Corp.); Inhibitors of protein tyrosine phosphatase. WO 9911606 .
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) 39328 (2S)-2-[[(benzyloxy)carbonyl]amino]-3-(4-hydroxyphenyl)propionic acid C17H17NO5 详情 详情
(II) 15764 amylamine; 1-pentanamine; pentylamine 110-58-7 C5H13N 详情 详情
(III) 39329 benzyl (1S)-1-(4-hydroxybenzyl)-2-oxo-2-(pentylamino)ethylcarbamate C22H28N2O4 详情 详情
(IV) 39330 diethyl 2-chloromalonate 14064-10-9 C7H11ClO4 详情 详情
(V) 39331 diethyl 2-[4-[(2S)-2-[[(benzyloxy)carbonyl]amino]-3-oxo-3-(pentylamino)propyl]phenoxy]malonate C29H38N2O8 详情 详情
(VI) 39332 diethyl 2-[4-[(2S)-2-amino-3-oxo-3-(pentylamino)propyl]phenoxy]malonate C21H32N2O6 详情 详情
(VII) 39333 diethyl 2-[4-[(2S)-2-isocyanato-3-oxo-3-(pentylamino)propyl]phenoxy]malonate C22H30N2O7 详情 详情
(VIII) 32593 ethyl (2S)-2-amino-3-phenylpropanoate C11H15NO2 详情 详情
(IX) 39334 diethyl 2-[4-[(2S)-2-[([[(1S)-1-benzyl-2-ethoxy-2-oxoethyl]amino]carbonyl)amino]-3-oxo-3-(pentylamino)propyl]phenoxy]malonate C33H45N3O9 详情 详情
Extended Information