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【结 构 式】

【分子编号】31808

【品名】tert-butyl (1R)-3-[benzyl(3-cyanopropyl)amino]-1-methylpropylcarbamate

【CA登记号】

【 分 子 式 】C20H31N3O2

【 分 子 量 】345.48516

【元素组成】C 69.53% H 9.04% N 12.16% O 9.26%

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:(X)

D-Alaninol (I) was protected as the tert-butyl carbamate (II) and then converted to mesylate (III). Displacement of the mesylate group of (III) with NaCN furnished nitrile (IV), which was hydrogenated over Raney Nickel to give diamine (V). Condensation of (V) with benzaldehyde (VI) in the presence of molecular sieves produced imine (VII) and subsequent reduction by means of NaBH4 gave rise to the benzyl amine (VIII). This amine was alkylated with 4-chlorobutyronitrile (IX) to afford nitrile (X), which was further converted to the triamino compound (XI) by hydrogenation over Raney Nickel. Reaction of (XI) with methyl 2-[(phenoxycarbonyl)oxy]acetate (XII) provided carbamate (XIII). The ester group of (XIII) was then hydrolyzed with NaOH to give carboxylic acid (XIV).

1 Lebreton, L.; et al.; Structure - Immunosuppressive activity relationships of new analogues of 15-deoxyspergualin. 2. Structural modifications of the spermidine moiety. J Med Chem 1999, 42, 23, 4749.
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) 21414 (2R)-2-Amino-1-propanol; D-Alaninol; D-(-)-Alaninol 35320-23-1 C3H9NO 详情 详情
(II) 31758 tert-butyl (1R)-2-hydroxy-1-methylethylcarbamate C8H17NO3 详情 详情
(III) 31803 (2R)-2-[(tert-butoxycarbonyl)amino]propyl methanesulfonate C9H19NO5S 详情 详情
(IV) 31804 tert-butyl (1R)-2-cyano-1-methylethylcarbamate C9H16N2O2 详情 详情
(V) 31805 tert-butyl (1R)-3-amino-1-methylpropylcarbamate C9H20N2O2 详情 详情
(VI) 10498 Benzaldehyde;Benzoic aldehyde;Phenylmethanal 100-52-7 C7H6O 详情 详情
(VII) 31806 tert-butyl (1R)-1-methyl-3-[[(E)-benzylidene]amino]propylcarbamate C16H24N2O2 详情 详情
(VIII) 31807 tert-butyl (1R)-3-(benzylamino)-1-methylpropylcarbamate C16H26N2O2 详情 详情
(IX) 11179 4-Chlorobutanenitrile; 4-Chlorobutyronitrile 628-20-6 C4H6ClN 详情 详情
(X) 31808 tert-butyl (1R)-3-[benzyl(3-cyanopropyl)amino]-1-methylpropylcarbamate C20H31N3O2 详情 详情
(XI) 31809 tert-butyl (1R)-3-[(4-aminobutyl)(benzyl)amino]-1-methylpropylcarbamate C20H35N3O2 详情 详情
(XII) 22341 methyl 2-[(phenoxycarbonyl)oxy]acetate C10H10O5 详情 详情
(XIII) 31810 methyl (6R)-9-benzyl-2,2,6-trimethyl-4,15-dioxo-3,16-dioxa-5,9,14-triazaoctadecan-18-oate C24H39N3O6 详情 详情
(XIV) 31811 (6R)-9-benzyl-2,2,6-trimethyl-4,15-dioxo-3,16-dioxa-5,9,14-triazaoctadecan-18-oic acid C23H37N3O6 详情 详情
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