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【结 构 式】 
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【分子编号】34631 【品名】2-methyl-2-phenylpropylamine; 2-methyl-2-phenyl-1-propanamine 【CA登记号】 |
【 分 子 式 】C10H15N 【 分 子 量 】149.23584 【元素组成】C 80.48% H 10.13% N 9.39% |
合成路线1
该中间体在本合成路线中的序号：(IX)The alkylation of (R)-alpha-methylbenzylamine (I) with methyl bromoacetate (II) gave aminoacetate (III). This was coupled with protected histidine (IV) by means of HATU as the coupling agent, yielding the protected dipeptide (V). Subsequent saponification of (V) using LiOH gave acid (VI). beta,beta-Dimethyl-phenethylamine (IX) was prepared by alkylation of phenylacetonitrile (VII) with iodomethane and NaH, followed by hydrogenation of the resulting dimethylated compound (VIII) in the presence of Raney Nickel. Coupling of amine (IX) with dipeptide (VI) provided the corresponding amide (X). The trityl protecting group of (X) was finally removed by treatment with trifluoroacetic acid.
| 【1】 Doherty, A.M.; Quin, J. III; Kaltenbronn, J.S.; Leonard, D.M.; McNamara, D.J. (Pfizer Inc.); Functionalized alkyl and alkenyl side chain derivs. of glycinamides as farnesyl transferase inhibitors. WO 9955725 . |
| 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) | 10039 | (1R)-1-Phenylethylamine; (1R)-1-Phenyl-1-ethanamine.; L-alpha-Phenylethylamine | 3886-69-9 | C8H11N | 详情 | 详情 |
| (II) | 12309 | methyl 2-bromoacetate; methyl bromoacetate | 96-32-2 | C3H5BrO2 | 详情 | 详情 |
| (III) | 34626 | methyl 2-[[(1R)-1-phenylethyl]amino]acetate | C11H15NO2 | 详情 | 详情 | |
| (IV) | 34627 | (2S)-2-[[(benzyloxy)carbonyl]amino]-3-(1-trityl-1H-imidazol-4-yl)propionic acid | C33H29N3O4 | 详情 | 详情 | |
| (V) | 34628 | methyl 2-[[(2S)-2-[[(benzyloxy)carbonyl]amino]-3-(1-trityl-1H-imidazol-4-yl)propanoyl][(1R)-1-phenylethyl]amino]acetate | C44H42N4O5 | 详情 | 详情 | |
| (VI) | 34629 | 2-[[(2S)-2-[[(benzyloxy)carbonyl]amino]-3-(1-trityl-1H-imidazol-4-yl)propanoyl][(1R)-1-phenylethyl]amino]acetic acid | C43H40N4O5 | 详情 | 详情 | |
| (VII) | 17046 | Phenylacetonitrile; 2-phenylacetonitrile; Benzyl cyanide | 140-29-4 | C8H7N | 详情 | 详情 |
| (VIII) | 34630 | 2-methyl-2-phenylpropanenitrile | C10H11N | 详情 | 详情 | |
| (IX) | 34631 | 2-methyl-2-phenylpropylamine; 2-methyl-2-phenyl-1-propanamine | C10H15N | 详情 | 详情 | |
| (X) | 34632 | benzyl (1S)-2-[[2-[(2-methyl-2-phenylpropyl)amino]-2-oxoethyl][(1R)-1-phenylethyl]amino]-2-oxo-1-[(1-trityl-1H-imidazol-4-yl)methyl]ethylcarbamate | C53H53N5O4 | 详情 | 详情 |