【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% |
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 |