methyl (2S)-2-[[chloro(phenoxy)phosphoryl]amino]propanoate -Drug Synthesis Database

【结构式】

【分子编号】41417

【品名】methyl (2S)-2-[[chloro(phenoxy)phosphoryl]amino]propanoate

【CA登记号】

【分子式】C₁₀H₁₃ClNO₄P

【分子量】277.644022

【元素组成】C 43.26% H 4.72% Cl 12.77% N 5.04% O 23.05% P 11.16%

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：(II)

The title compound was synthesized by coupling 5-(bromovinyl)-2'-deoxyuridine (I) with phenyl L-methoxyalanino phosphoroamidate (II) in the presence of imidazole in DMF.

参考文献中间体

合成目标

【1】 Vaino, A.R.; Lobl, T.J.; Baehr, D.N.; Lehsten, D.M.; An improved procedure for the synthesis of nucleoside phosphoramidates. Org Process Res Dev 2002, 6, 6, 819.
【2】 Shepard, H.M. (NewBiotics, Inc.); Enzyme catalyzed therapeutic agents. EP 1167972; JP 2001220397; US 6245750; WO 9937753 .

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)	49856	5-[(E)-2-bromoethenyl]-1-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)tetrahydro-2-furanyl]-2,4(1H,3H)-pyrimidinedione		C₁₁H₁₃BrN₂O₅	详情	详情
(II)	41417	methyl (2S)-2-[[chloro(phenoxy)phosphoryl]amino]propanoate		C₁₀H₁₃ClNO₄P	详情	详情

合成路线2

该中间体在本合成路线中的序号：(III)

The reaction of 6-chloro-9-[2-(hydroxymethyl)cyclopropylidenemethyl]purine-2-amine (I) with methanol and K2CO3 gives of 9-[2-(hydroxymethyl)cyclopropylidenemethyl]-6-methoxypurine-2-amine (II) which is then condensed with the phosphorylated L-alanine ester (III) by means of N-methylimidazole (NMI) in pyridine/THF. The intermediate the phosphorylated L-alanine ester (III) has been obtained by condensation of L-alanine methyl ester (IV) with phenyl dichlorophosphate (V) by means of TEA in dichloromethane.

参考文献中间体

合成目标

【1】 Kern, E.R.; Qiu, Y.-L.; Ptak, R.G.; Breitenbach, J.M.; Zemlicka, J.; Drach, J.C.; Cheng, Y.-C.; Lin, J.-S.; Synthesis and antiviral activity of phosphoralaninate derivatives of methylenecyclopropane analogues of nucleosides. Antivir Res 1999, 43, 1, 37.

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)	41415	[2-[(Z)-(2-amino-6-chloro-9H-purin-9-yl)methylidene]cyclopropyl]methanol		C₁₀H₁₀ClN₅O	详情	详情
(II)	41416	[2-[(Z)-(2-amino-6-methoxy-9H-purin-9-yl)methylidene]cyclopropyl]methanol		C₁₁H₁₃N₅O₂	详情	详情
(III)	41417	methyl (2S)-2-[[chloro(phenoxy)phosphoryl]amino]propanoate		C₁₀H₁₃ClNO₄P	详情	详情
(IV)	20694	methyl (2S)-2-aminopropanoate		C₄H₉NO₂	详情	详情
(V)	39640	Phenyl dichlorophosphate;phenyl phosphorodichloridate	770-12-7	C₆H₅Cl₂O₂P	详情	详情

Extended Information