methyl 2-[3-(2-pyridinyl)phenyl]acetate -Drug Synthesis Database

【结构式】

【分子编号】50903

【品名】methyl 2-[3-(2-pyridinyl)phenyl]acetate

【CA登记号】

【分子式】C₁₄H₁₃NO₂

【分子量】227.26276

【元素组成】C 73.99% H 5.77% N 6.16% O 14.08%

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：(III)

Palladium-catalyzed coupling of methyl (3-bromophenyl)acetate (I) with 2-pyridyl triflate (II) furnished the pyridylphenylacetate ester (III), which was further hydrolyzed with LiOH to the corresponding carboxylic acid (IV). Coupling of acid (IV) with (3S)-3N-Boc-1,3-diamino-2-butanol (V) using HBTU produced amide (VI). After acid cleavage of the Boc protecting group of (VI), the resulting amine (VII) was coupled with N-Boc-leucine (VIII), yielding adduct (IX). Subsequent acidic deprotection of (IX) provided the intermediate amine (X).

参考文献中间体

合成目标

【1】 Bondinell, W.E.; Desjarlais, R.L.; Yamashita, D.S.; Veber, D.F. (GlaxoSmithKline Inc.); Protease inhibitors. WO 9959526 .

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)	50901	methyl 2-(3-bromophenyl)acetate	150529-73-0	C₉H₉BrO₂	详情	详情
(II)	50902	2-Pyridyl trifluoromethanesulfonate; 2-Pyridyl triflate		C₆H₄F₃NO₃S	详情	详情
(III)	50903	methyl 2-[3-(2-pyridinyl)phenyl]acetate		C₁₄H₁₃NO₂	详情	详情
(IV)	50904	2-[3-(2-pyridinyl)phenyl]acetic acid		C₁₃H₁₁NO₂	详情	详情
(V)	50905	tert-butyl (1S)-3-amino-2-hydroxy-1-methylpropylcarbamate		C₉H₂₀N₂O₃	详情	详情
(VI)	50906	tert-butyl (1S)-2-hydroxy-1-methyl-3-([2-[3-(2-pyridinyl)phenyl]acetyl]amino)propylcarbamate		C₂₂H₂₉N₃O₄	详情	详情
(VII)	50907	N-[(3S)-3-amino-2-hydroxybutyl]-2-[3-(2-pyridinyl)phenyl]acetamide		C₁₇H₂₁N₃O₂	详情	详情
(VIII)	23663	(2S)-2-[(tert-butoxycarbonyl)amino]-4-methylpentanoic acid；N-Boc-L-leucine		C₁₁H₂₁NO₄	详情	详情
(IX)	50908	tert-butyl (1S)-1-([[(1S)-2-hydroxy-1-methyl-3-([2-[3-(2-pyridinyl)phenyl]acetyl]amino)propyl]amino]carbonyl)-3-methylbutylcarbamate		C₂₈H₄₀N₄O₅	详情	详情
(X)	50909	(2S)-2-amino-N-[(1S)-2-hydroxy-1-methyl-3-([2-[3-(2-pyridinyl)phenyl]acetyl]amino)propyl]-4-methylpentanamide		C₂₃H₃₂N₄O₃	详情	详情

Extended Information