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【结 构 式】

【分子编号】49983

【品名】(2S)-2-[((2S)-2-[[(benzyloxy)carbonyl]amino]-3-methylbutanoyl)amino]-4-(tert-butoxy)-4-oxobutyric acid

【CA登记号】

【 分 子 式 】C21H30N2O7

【 分 子 量 】422.47848

【元素组成】C 59.7% H 7.16% N 6.63% O 26.51%

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:(III)

Aspartic acid beta-tert-butyl ester (II) was silylated using bis(trimethylsilyl)acetamide and subsequently coupled with the hydroxysuccinimidyl ester of Z-valine (I) to furnish dipeptide (III) (1). This was converted to the corresponding mixed anhydride (IV) with isobutyl chloroformate and N-methylmorpholine. Reaction of anhydride (IV) with ethereal diazomethane, followed by treatment of the intermediate diazo ketone with HBr in HOAc, gave rise to the bromo ketone (V). Tetrafluorophenol (VI) was alkylated with bromide (V) to yield ether (VII). The ketone function of (VII) was then reduced to alcohol (VIII) employing NaBH4. Further hydrogenolysis of the benzyloxycarbonyl group of (VIII) provided amine (IX).

1 Ternansky, R.J.; et al.; Structure-activity relationship of a series of oxamyl dipeptide caspase inhibitors developed for the treatment of stroke. 221st ACS Natl Meet (April 1 2001, San Diego) 2001, Abst MEDI 75.
2 Karanewsky, D.S.; Ternansky, R.J. (Idun Pharmaceuticals, Inc.); C-Terminal modified oxamyl dipeptides as inhibitors of the ICE/ced-3 family of cysteine proteases. EP 1091930; WO 0001666 .
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) 49982 benzyl (1S)-1-[[(2,5-dioxo-1-pyrrolidinyl)oxy]carbonyl]-2-methylpropylcarbamate C17H20N2O6 详情 详情
(II) 26564 (2S)-2-amino-4-(tert-butoxy)-4-oxobutyric acid 3057-74-7 C8H15NO4 详情 详情
(III) 49983 (2S)-2-[((2S)-2-[[(benzyloxy)carbonyl]amino]-3-methylbutanoyl)amino]-4-(tert-butoxy)-4-oxobutyric acid C21H30N2O7 详情 详情
(IV) 49984   C26H38N2O9 详情 详情
(V) 49985 tert-butyl (3S)-3-[((2S)-2-[[(benzyloxy)carbonyl]amino]-3-methylbutanoyl)amino]-5-bromo-4-oxopentanoate C22H31BrN2O6 详情 详情
(VI) 49986 2,3,5,6-Tetrafluorophenol 769-39-1 C6H2F4O 详情 详情
(VII) 49987 tert-butyl (3S)-3-[((2S)-2-[[(benzyloxy)carbonyl]amino]-3-methylbutanoyl)amino]-4-oxo-5-(2,3,5,6-tetrafluorophenoxy)pentanoate C28H32F4N2O7 详情 详情
(VIII) 49988 tert-butyl (3S)-3-[((2S)-2-[[(benzyloxy)carbonyl]amino]-3-methylbutanoyl)amino]-4-hydroxy-5-(2,3,5,6-tetrafluorophenoxy)pentanoate C28H34F4N2O7 详情 详情
(IX) 49989 tert-butyl (3S)-3-[[(2S)-2-amino-3-methylbutanoyl]amino]-4-hydroxy-5-(2,3,5,6-tetrafluorophenoxy)pentanoate C20H28F4N2O5 详情 详情
Extended Information