ethyl (2S)-2-amino-3-phenylpropanoate -Drug Synthesis Database

【结构式】

【分子编号】32593

【品名】ethyl (2S)-2-amino-3-phenylpropanoate

【CA登记号】

【分子式】C₁₁H₁₅NO₂

【分子量】193.24564

【元素组成】C 68.37% H 7.82% N 7.25% O 16.56%

与该中间体有关的原料药合成路线共 2 条

合成路线1 合成路线2

合成路线1

该中间体在本合成路线中的序号：(V)

Mitsunobu coupling of 2-(4-methylpiperazin-1-yl)ethanol (I) with 3,5-dichloro-2,4-dihydroxybenzoic acid (II) in the presence of diisopropyl azodicarboxylate and triphenylphosphine afforded ether (III). Subsequent hydrolysis of the methyl ester group of (III) provided acid (IV), which was coupled with L-phenylalanine methyl ester-HCl (V) employing EDC and HOBt. The title compound was finally isolated as the corresponding dihydrochloride salt.

参考文献中间体

合成目标

【1】 Haruta, J.; Sakuma, K.; Watanabe, Y. (Japan Tobacco Inc.); Amide compounds and use of the same. EP 0849256 .

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)	32589	2-(4-methyl-1-piperazinyl)-1-ethanol	5464-12-0	C₇H₁₆N₂O	详情	详情
(II)	32590	methyl 3,5-dichloro-2,4-dihydroxybenzoate		C₈H₆Cl₂O₄	详情	详情
(III)	32591	methyl 3,5-dichloro-2-hydroxy-4-[2-(4-methyl-1-piperazinyl)ethoxy]benzoate		C₁₅H₂₀Cl₂N₂O₄	详情	详情
(IV)	32592	3,5-dichloro-2-hydroxy-4-[2-(4-methyl-1-piperazinyl)ethoxy]benzoic acid		C₁₄H₁₈Cl₂N₂O₄	详情	详情
(V)	32593	ethyl (2S)-2-amino-3-phenylpropanoate		C₁₁H₁₅NO₂	详情	详情

合成路线2

该中间体在本合成路线中的序号：(VIII)

Coupling of N-Cbz-tyrosine (I) with n-pentylamine (II) afforded amide (III). Subsequent alkylation of the phenol group of (III) with diethyl chloromalonate (IV) gave phenoxy malonate (V). Hydrogenolytical deprotection of the N-Cbz group of (V) provided the corresponding amine, which was isolated as the hydrochloride salt (VI). Conversion of (VI) to isocyanate (VII) was effected by treatment with diphosgene in the presence of Proton Sponge(r). Addition of phenylalanine ethyl ester (VIII) to isocyanate (VII) furnished urea (IX). Finally, the ethyl ester groups of (IX) were saponified with LiOH to yield the title compound.

参考文献中间体

合成目标

【1】 Bleasdale, J.; May, P.D.; Schostarez, H.J.; Barf, T.; Larsen, S.D.; Liljebris, C. (Pharmacia Corp.); Inhibitors of protein tyrosine phosphatase. WO 9911606 .

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)	39328	(2S)-2-[[(benzyloxy)carbonyl]amino]-3-(4-hydroxyphenyl)propionic acid		C₁₇H₁₇NO₅	详情	详情
(II)	15764	amylamine; 1-pentanamine; pentylamine	110-58-7	C₅H₁₃N	详情	详情
(III)	39329	benzyl (1S)-1-(4-hydroxybenzyl)-2-oxo-2-(pentylamino)ethylcarbamate		C₂₂H₂₈N₂O₄	详情	详情
(IV)	39330	diethyl 2-chloromalonate	14064-10-9	C₇H₁₁ClO₄	详情	详情
(V)	39331	diethyl 2-[4-[(2S)-2-[[(benzyloxy)carbonyl]amino]-3-oxo-3-(pentylamino)propyl]phenoxy]malonate		C₂₉H₃₈N₂O₈	详情	详情
(VI)	39332	diethyl 2-[4-[(2S)-2-amino-3-oxo-3-(pentylamino)propyl]phenoxy]malonate		C₂₁H₃₂N₂O₆	详情	详情
(VII)	39333	diethyl 2-[4-[(2S)-2-isocyanato-3-oxo-3-(pentylamino)propyl]phenoxy]malonate		C₂₂H₃₀N₂O₇	详情	详情
(VIII)	32593	ethyl (2S)-2-amino-3-phenylpropanoate		C₁₁H₁₅NO₂	详情	详情
(IX)	39334	diethyl 2-[4-[(2S)-2-[([[(1S)-1-benzyl-2-ethoxy-2-oxoethyl]amino]carbonyl)amino]-3-oxo-3-(pentylamino)propyl]phenoxy]malonate		C₃₃H₄₅N₃O₉	详情	详情

Extended Information