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【结 构 式】

【分子编号】47879

【品名】9H-fluoren-9-ylmethyl (1S)-1-[(1S)-2-amino-1-hydroxy-2-oxoethyl]pentylcarbamate

【CA登记号】

【 分 子 式 】C22H26N2O4

【 分 子 量 】382.45952

【元素组成】C 69.09% H 6.85% N 7.32% O 16.73%

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 resin-bound aminohydroxyacid (IX) was prepared as follows. 2-Heptenoic acid (I) was converted to the corresponding tert-butyl ester (II) upon treatment with dimethylformamide di-tert-butylacetal. Conjugate addition to (II) of the chiral amine (III) followed by oxidative treatment with (+)-(camphorsulfonyl)oxaziridine then furnished the amino hydroxyester (IV). Hydrogenolytic cleavage of the N-benzyl groups of (IV) produced the primary amine (V), which was subsequently protected as the N-Fmoc derivative (VI) by using O-Fmoc-hydroxysuccinimide. Tert-butyl ester cleavage in (VI) by means of trifluoroacetic acid gave carboxylic acid (VII). This was then attached to Rink resin using TBTU as the coupling reagent to yield resin (VIII). Deprotection of the N-Fmoc group of (VIII) with piperidine in DMF produced the resin-bound aminohydroxyacid (IX).

1 Jones, P.S.; Kay, P.B.; Wilson, F.X.; Raynham, T.M.; Hurst, D.N. (Hoffmann-La Roche, Inc.); alpha-Ketoamide derivs.. US 6187905 .
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) 47873 (E)-2-heptenoic acid 10352-88-2 C7H12O2 详情 详情
(II) 47874 tert-butyl (E)-2-heptenoate C11H20O2 详情 详情
(III) 47881 (1R)-N-benzyl-1-phenyl-1-ethanamine; N-benzyl-N-[(1R)-1-phenylethyl]amine C15H17N 详情 详情
(IV) 47875 tert-butyl (2S,3S)-3-[benzyl[(1R)-1-phenylethyl]amino]-2-hydroxyheptanoate C26H37NO3 详情 详情
(V) 47876 tert-butyl (2S,3S)-3-amino-2-hydroxyheptanoate C11H23NO3 详情 详情
(VI) 47877 tert-butyl (2S,3S)-3-[[(9H-fluoren-9-ylmethoxy)carbonyl]amino]-2-hydroxyheptanoate C26H33NO5 详情 详情
(VII) 47878 (2S,3S)-3-[[(9H-fluoren-9-ylmethoxy)carbonyl]amino]-2-hydroxyheptanoic acid C22H25NO5 详情 详情
(VIII) 47879 9H-fluoren-9-ylmethyl (1S)-1-[(1S)-2-amino-1-hydroxy-2-oxoethyl]pentylcarbamate C22H26N2O4 详情 详情
(IX) 47880 (2S,3S)-3-amino-2-hydroxyheptanamide C7H16N2O2 详情 详情
Extended Information