【结 构 式】 |
【分子编号】52632 【品名】1,1-dimethylethyl 1-[5-oxo-4-(phenylmethylidene)tetrahydro-2-furanyl]-2-phenylethylcarbamate 【CA登记号】 |
【 分 子 式 】C24H27NO4 【 分 子 量 】393.48272 【元素组成】C 73.26% H 6.92% N 3.56% O 16.26% |
合成路线1
该中间体在本合成路线中的序号:(III)The alkylation of N-[1(S)-(5-oxotetrahydrofuran-2(R)-yl)-2-phenylethyl]carbamic acid tert-butyl ester (I) with benzaldehyde (II) by means of LDA in THF, followed by a treatment with Ac2O and TEA at 120 C, gives the benzylidene derivative (III), which is hydrogenated with H2 over Pd/C in methanol/ethyl acetate to yield N-[1(S)-[4(R)-benzyl-5-oxotetrahydrofuran-2(R)-yl]-2-phenylethyl]carbamic acid tert-butyl ester (IV). The hydrolysis of (IV) with NaOH in dimethoxyethane/water affords the hexanoic acid (V), which is finally condensed with the dipeptide L-leucyl-L-phenylalaninamide (VI) by means of EDC and HOBT in DMF to provide the target acylated dipeptide.
【1】 Hunt, P.A.; Harrison, T.; Castro Pineiro, J.L.; Nadin, A.J. (Merck Sharp & Dohme Ltd.); gamma-Secretase inhibitors. WO 0153255 . |
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) | 52631 | 1,1-dimethylethyl 1-(5-oxotetrahydro-2-furanyl)-2-phenylethylcarbamate | C17H23NO4 | 详情 | 详情 | |
(II) | 10498 | Benzaldehyde;Benzoic aldehyde;Phenylmethanal | 100-52-7 | C7H6O | 详情 | 详情 |
(III) | 52632 | 1,1-dimethylethyl 1-[5-oxo-4-(phenylmethylidene)tetrahydro-2-furanyl]-2-phenylethylcarbamate | C24H27NO4 | 详情 | 详情 | |
(IV) | 52633 | 1,1-dimethylethyl 1-[5-oxo-4-(phenylmethyl)tetrahydro-2-furanyl]-2-phenylethylcarbamate | C24H29NO4 | 详情 | 详情 | |
(V) | 52634 | 5-({[(1,1-dimethylethyl)oxy]carbonyl}amino)-4-hydroxy-6-phenyl-2-(phenylmethyl)hexanoic acid | C24H31NO5 | 详情 | 详情 | |
(VI) | 52635 | 2-amino-N-[2-amino-2-oxo-1-(phenylmethyl)ethyl]-4-methylpentanamide | C15H23N3O2 | 详情 | 详情 |