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【结 构 式】

【分子编号】60792

【品名】benzyl (Z)-{4-[(2S)-2-[((2R,3S)-3-{[(benzyloxy)amino]carbonyl}-2-isobutyl-6-phenylhexanoyl)amino]-3-(methylamino)-3-oxopropyl]anilino}{[(benzyloxy)carbonyl]amino}methylidenecarbamate

【CA登记号】

【 分 子 式 】C51H58N6O8

【 分 子 量 】883.05716

【元素组成】C 69.37% H 6.62% N 9.52% O 14.49%

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:(XIV)

N-Boc-L-4'-Aminophenylalanine-N-methylamide (VIII) was converted to the guanidine derivative (X) by reaction with pyrazole-N,N'-bis(benzyloxycarbonyl)carboxamidine (IX). After acidic Boc group cleavage in (IX), the resultant amino amide (XI) was coupled with the carboxylic acid (VII) to produce a diastereomeric mixture of amides, which were separated by column chromatography. The desired isomer (XII) was then treated with 95% aqueous trifluoroacetic acid to remove the tert-butyl ester group, yielding acid (XIII). Coupling of (XIII) with O-benzyl hydroxylamine furnished the O-benzyl hydroxamate (XIV). Finally, the benzyl and benzyloxycarbonyl protecting groups of (XIV) were removed by catalytic hydrogenation over Pd/C to afford the title compound.

1 Fujisawa, T.; Odake, S.; Morita, Y.; Hongo, T.; Ito, H.; Yasuda, J.; Suda, E.; Igeta, K.; Morikawa, T. (Fuji Yakuhin Kogyo Co., Ltd.); Highly water-soluble metalloproteinase inhibitor. EP 0832875; WO 9633968 .
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(VII) 60699 (2R)-3-(tert-butoxycarbonyl)-2-isobutyl-6-phenylhexanoic acid C21H32O4 详情 详情
(VIII) 60700 tert-butyl (1S)-1-(4-aminobenzyl)-2-(methylamino)-2-oxoethylcarbamate C15H23N3O3 详情 详情
(IX) 60787   C6H10N4 详情 详情
(X) 60788 benzyl (Z)-{[(benzyloxy)carbonyl]amino}{4-[(2S)-2-[(tert-butoxycarbonyl)amino]-3-(methylamino)-3-oxopropyl]anilino}methylidenecarbamate C32H37N5O7 详情 详情
(XI) 60789 benzyl (Z)-{4-[(2S)-2-amino-3-(methylamino)-3-oxopropyl]anilino}{[(benzyloxy)carbonyl]amino}methylidenecarbamate C27H29N5O5 详情 详情
(XII) 60790 tert-butyl (2S,3R)-3-({[(1S)-1-{4-[({[(benzyloxy)carbonyl]amino}{[(benzyloxy)carbonyl]imino}methyl)amino]benzyl}-2-(methylamino)-2-oxoethyl]amino}carbonyl)-5-methyl-2-(3-phenylpropyl)hexanoate C48H59N5O8 详情 详情
(XIII) 60791 (2S,3R)-3-({[(1S)-1-{4-[({[(benzyloxy)carbonyl]amino}{[(benzyloxy)carbonyl]imino}methyl)amino]benzyl}-2-(methylamino)-2-oxoethyl]amino}carbonyl)-5-methyl-2-(3-phenylpropyl)hexanoic acid C44H51N5O8 详情 详情
(XIV) 60792 benzyl (Z)-{4-[(2S)-2-[((2R,3S)-3-{[(benzyloxy)amino]carbonyl}-2-isobutyl-6-phenylhexanoyl)amino]-3-(methylamino)-3-oxopropyl]anilino}{[(benzyloxy)carbonyl]amino}methylidenecarbamate C51H58N6O8 详情 详情
Extended Information