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【结 构 式】

【分子编号】46852

【品名】benzyl (4R)-4-[(2,2-diphenylacetyl)amino]-5-[[(1R)-1-(4-hydroxyphenyl)ethyl]amino]-5-oxopentylcarbamate

【CA登记号】

【 分 子 式 】C35H37N3O5

【 分 子 量 】579.696

【元素组成】C 72.52% H 6.43% N 7.25% O 13.8%

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:(VIII)

The protected (R)-ornithine (I) was converted to the active ester (III) upon coupling with 2-nitrophenol (II) in the presence of DCC and pyridine. Subsequent reaction of the nitrophenyl ester (III) with (R)-4-hydroxy-alpha-methylbenzylamine (IV) produced the corresponding amide (V). After acid cleavage of the Boc protecting group of (V), the resulting amine (VI) was acylated with diphenylacetyl chloride (VII) to give (VIII). Removal of the N-benzyloxycarbonyl group of (VIII) was achieved by catalytic hydrogenation over Pd/C. The resultant amine (IX) was then converted to the protected guanidine (XI) by reaction with N,N'-bis(benzyloxycarbonyl)-S-methylisothiourea (X). The protecting groups of (X) were finally removed by hydrogenation over Pd/C.

1 Pilling, G.; Bergman, N.-A.; D'Ambra, T. (AstraZeneca plc); New NPY antagonists. EP 1017672; WO 9915498 .
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) 44215 (2R)-5-[[(benzyloxy)carbonyl]amino]-2-[(tert-butoxycarbonyl)amino]pentanoic acid C18H26N2O6 详情 详情
(II) 19106 2-nitrophenol 88-75-5 C6H5NO3 详情 详情
(III) 46848 2-nitrophenyl (2R)-5-[[(benzyloxy)carbonyl]amino]-2-[(tert-butoxycarbonyl)amino]pentanoate C24H29N3O8 详情 详情
(IV) 46849 4-[(1R)-1-aminoethyl]phenol 134855-87-1 C8H11NO 详情 详情
(V) 46850 benzyl (4R)-4-[(tert-butoxycarbonyl)amino]-5-[[(1R)-1-(4-hydroxyphenyl)ethyl]amino]-5-oxopentylcarbamate C26H35N3O6 详情 详情
(VI) 46851 benzyl (4R)-4-amino-5-[[(1R)-1-(4-hydroxyphenyl)ethyl]amino]-5-oxopentylcarbamate C21H27N3O4 详情 详情
(VII) 23800 Diphenylacetyl chloride; 2,2-diphenylacetyl chloride 1871-76-7 C14H11ClO 详情 详情
(VIII) 46852 benzyl (4R)-4-[(2,2-diphenylacetyl)amino]-5-[[(1R)-1-(4-hydroxyphenyl)ethyl]amino]-5-oxopentylcarbamate C35H37N3O5 详情 详情
(IX) 46853 (2R)-5-amino-2-[(2,2-diphenylacetyl)amino]-N-[(1R)-1-(4-hydroxyphenyl)ethyl]pentanamide C27H31N3O3 详情 详情
(X) 32861 benzyl (E)-[[(benzyloxy)carbonyl]amino](methylsulfanyl)methylidenecarbamate C18H18N2O4S 详情 详情
(XI) 46854 benzyl (E)-[[(benzyloxy)carbonyl]amino][((4R)-4-[(2,2-diphenylacetyl)amino]-5-[[(1R)-1-(4-hydroxyphenyl)ethyl]amino]-5-oxopentyl)amino]methylidenecarbamate C44H45N5O7 详情 详情
Extended Information