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【结 构 式】 
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【分子编号】43760 【品名】methyl (2S)-2-[([5-[([(1S)-2-cyclohexyl-1-[(ethylsulfanyl)methyl]ethyl]amino)methyl]-2'-methyl[1,1'-biphenyl]-2-yl]carbonyl)amino]-4-(methylsulfanyl)butanoate 【CA登记号】 |
【 分 子 式 】C32H46N2O3S2 【 分 子 量 】570.86092 【元素组成】C 67.33% H 8.12% N 4.91% O 8.41% S 11.23% |
合成路线1
该中间体在本合成路线中的序号：(XI)Palladium-catalyzed coupling of dimethyl iodoterephthalate (I) with 2-methylphenylboronic acid (II) furnished the biphenyl derivative (III). Regioselective ester hydrolysis of (III) under controlled conditions provided the mono acid (IV), which was further reduced to alcohol (V) using borane in THF. After hydrolysis of the remaining ester function of (V), the resulting carboxylic acid (VI) was coupled to L-methionine methyl ester (VII), yielding amide (VIII). Swern oxidation of the alcohol function of (VIII) gave aldehyde (IX). This was then subjected to a reductive amination with amine (X) in the presence of NaBH(OAc)3 to afford the secondary amine (XI). The methyl ester group of (XI) was finally hydrolyzed with LiOH.
| 【1】 Tasker, A.S.; Wasicak, J.; Henry, K.J. Jr.; et al.; PDB-093. Drug Data Rep 1995, 17, 2, 138. |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (VIIII) | 43757 | methyl (2S)-2-([[5-(hydroxymethyl)-2'-methyl[1,1'-biphenyl]-2-yl]carbonyl]amino)-4-(methylsulfanyl)butanoate | C21H25NO4S | 详情 | 详情 | |
| (I) | 38996 | dimethyl 2-iodoterephthalate | C10H9IO4 | 详情 | 详情 | |
| (II) | 38997 | 2-methylphenylboronic acid | 16419-60-6 | C7H9BO2 | 详情 | 详情 |
| (III) | 38998 | dimethyl 2'-methyl[1,1'-biphenyl]-2,5-dicarboxylate | C17H16O4 | 详情 | 详情 | |
| (IV) | 38999 | 6-(methoxycarbonyl)-2'-methyl[1,1'-biphenyl]-3-carboxylic acid | C16H14O4 | 详情 | 详情 | |
| (V) | 39000 | methyl 5-(hydroxymethyl)-2'-methyl[1,1'-biphenyl]-2-carboxylate | C16H16O3 | 详情 | 详情 | |
| (VI) | 43756 | 5-(hydroxymethyl)-2'-methyl[1,1'-biphenyl]-2-carboxylic acid | C15H14O3 | 详情 | 详情 | |
| (VII) | 17950 | D-Methionine methyl ester; methyl (2S)-2-amino-4-(methylsulfanyl)butanoate hydrochloride | 21691-49-6 | C6H13NO2S | 详情 | 详情 |
| (IX) | 43758 | methyl (2S)-2-[[(5-formyl-2'-methyl[1,1'-biphenyl]-2-yl)carbonyl]amino]-4-(methylsulfanyl)butanoate | C21H23NO4S | 详情 | 详情 | |
| (X) | 43759 | (2S)-1-cyclohexyl-3-(ethylsulfanyl)-2-propanamine; (1S)-2-cyclohexyl-1-[(ethylsulfanyl)methyl]ethylamine | C11H23NS | 详情 | 详情 | |
| (XI) | 43760 | methyl (2S)-2-[([5-[([(1S)-2-cyclohexyl-1-[(ethylsulfanyl)methyl]ethyl]amino)methyl]-2'-methyl[1,1'-biphenyl]-2-yl]carbonyl)amino]-4-(methylsulfanyl)butanoate | C32H46N2O3S2 | 详情 | 详情 |