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【结 构 式】

【分子编号】43757

【品名】methyl (2S)-2-([[5-(hydroxymethyl)-2'-methyl[1,1'-biphenyl]-2-yl]carbonyl]amino)-4-(methylsulfanyl)butanoate

【CA登记号】

【 分 子 式 】C21H25NO4S

【 分 子 量 】387.49984

【元素组成】C 65.09% H 6.5% N 3.61% O 16.52% S 8.28%

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:(VIIII)

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
Extended Information