【结 构 式】 |
【分子编号】26167 【品名】(4S)-4-isopropyl-3-[2-(4-isopropylphenyl)acetyl]-1,3-oxazolidin-2-one 【CA登记号】 |
【 分 子 式 】C17H23NO3 【 分 子 量 】289.37456 【元素组成】C 70.56% H 8.01% N 4.84% O 16.59% |
合成路线1
该中间体在本合成路线中的序号:(III)The intermediate (S)-1-(4-isopropylphenyl)ethylamine (VII) was prepared as shown in Scheme 1. Condensation of (4-isopropylphenyl)acetyl chloride (I) with the lithium salt of (S)-4-isopropyl-2-oxazolidinone (II) produced the chiral N-acyl oxazolidinone (III). Diastereoselective alkylation of (III) with MeI in the presence of lithium hexamethyldisilazide provided (IV). Removal of the chiral auxiliary of (IV) was accomplished by treatment with lithium hydroperoxide to afford the (S)-arylpropionic acid (V). Subsequent Curtius rearrangement of (V) using diphenyl phosphoryl azide, followed by treatment of the intermediate isocyanate with benzyl alcohol, furnished the benzyl carbamate (VI). Then, catalytic hydrogenation of (VI) over Pd/C yielded the target amine (VII).
【1】 Llinas-Brunet, M.; et al.; Phosphotyrosine-containing dipeptides as high-affinity ligands for the p56lck SH2 domain. J Med Chem 1999, 42, 4, 722. |
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) | 26166 | 2-(4-isopropylphenyl)acetyl chloride | C11H13ClO | 详情 | 详情 | |
(II) | 12867 | (4S)-4-Isopropyl-1,3-oxazolidin-2-one; (R)-4-Isopropyl-2-oxazolidinone | 17016-83-0 | C6H11NO2 | 详情 | 详情 |
(III) | 26167 | (4S)-4-isopropyl-3-[2-(4-isopropylphenyl)acetyl]-1,3-oxazolidin-2-one | C17H23NO3 | 详情 | 详情 | |
(IV) | 26168 | (4S)-4-isopropyl-3-[(2S)-2-(4-isopropylphenyl)propanoyl]-1,3-oxazolidin-2-one | C18H25NO3 | 详情 | 详情 | |
(V) | 26169 | (2S)-2-(4-isopropylphenyl)propionic acid | C12H16O2 | 详情 | 详情 | |
(VI) | 26170 | benzyl (1S)-1-(4-isopropylphenyl)ethylcarbamate | C19H23NO2 | 详情 | 详情 | |
(VII) | 26171 | (1S)-1-(4-isopropylphenyl)ethylamine; (1S)-1-(4-isopropylphenyl)-1-ethanamine | C11H17N | 详情 | 详情 |