methyl 2,2,2-trichloroacetate -Drug Synthesis Database

【结构式】

【分子编号】62440

【品名】methyl 2,2,2-trichloroacetate

【CA登记号】598-99-2

【分子式】C₃H₃Cl₃O₂

【分子量】177.41372

【元素组成】C 20.31% H 1.7% Cl 59.95% O 18.04%

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：(XVI)

A new enantioselective method for the preparation of glycidic ester (XIV) has been disclosed. Methyl trichloroacetate (XVI) was converted to the dichloroketene silyl acetal (XVII) by treatment with zinc powder and chlorotrimethylsilane. Asymmetric aldol condensation of (XVII) with anisaldehyde (X) in the presence of the chiral oxazaborolidine catalyst (XVIII) at -78 C produced methyl (S)-2,2-dichloro-3-hydroxy-3-(4-methoxyphenyl)propionate (XIX). Reductive mono-dechlorination of (XIX) furnished chlorohydrin (XX), which was then cyclized to glycidic ester (XIV) in the presence of NaOMe

参考文献中间体

合成目标

【1】 Imashiro, R.; Kuroda, T.; Asymmetric synthesis of methyl (2R,3S)-3-(4-methoxyphenyl) glycidate, a key intermediate of diltiazem, via Mukaiyama aldol reaction. Tetrahedron Lett 2001, 42, 7, 1313.

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
(X)	27251	4-methoxybenzaldehyde; Anisicaldehyde; p-anisaldehyde	123-11-5	C₈H₈O₂	详情	详情
(XIV)	62435	ethyl (2R,3S)-3-(4-methoxyphenyl)-2-oxiranecarboxylate		C₁₂H₁₄O₄	详情	详情
(XVI)	62440	methyl 2,2,2-trichloroacetate	598-99-2	C₃H₃Cl₃O₂	详情	详情
(XVII)	62441			C₄H₆Cl₂O₂	详情	详情
(XVIII)	62442			C₆H₁₂BNO₂	详情	详情
(XIX)	62443	methyl (3S)-2,2-dichloro-3-hydroxy-3-(4-methoxyphenyl)propanoate		C₁₁H₁₂Cl₂O₄	详情	详情
(XX)	62444	methyl (3S)-2-chloro-3-hydroxy-3-(4-methoxyphenyl)propanoate		C₁₁H₁₃ClO₄	详情	详情

合成路线2

该中间体在本合成路线中的序号：(I)

参考文献中间体

合成目标

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
（VIII）	65680	N-Boc-(S)-(3-hydroxyadamantyl)glycine		C₁₇H₂₈NO₅	详情	详情
(I)	62440	methyl 2,2,2-trichloroacetate	598-99-2	C₃H₃Cl₃O₂	详情	详情
(II)	65698	1-Bromoadamantane; 1-Bromotricyclo[3.3.1.1(3,7)]decane; 1-Adamantyl bromide	768-90-1	C₁₀H₁₅Br	详情	详情
(III)	67428	methyl 2-(adamantan-1-yl)-2,2-dichloroacetate		C₁₃H₁₈Cl₂O₂	详情	详情
(IV)	67429	methyl 2,2-dichloro-2-(3-hydroxyadamantan-1-yl)acetate		C₁₃H₁₈Cl₂O₃	详情	详情
(V)	67430	2,2-dichloro-2-(3-hydroxyadamantan-1-yl)acetic acid		C₁₂H₁₆Cl₂O₃	详情	详情
(VI)	65703	2-(3-Hydroxy-1-adamantyl)-2-oxoacetic acid; 3-Hydroxy-alpha-oxotricyclo[3.3.1.1(3,7)]decane-1-acetic acid;	709031-28-7	C₁₂H₁₆O₄	详情	详情
(VII)	65681	(S)-(3-hydroxyadamantyl)glycine		C₁₂H₁₉NO₃	详情	详情
(IX)	67427	((2,2-dichloro-1-methoxyvinyl)oxy)trimethylsilane		C₆H₁₂Cl₂O₂Si	详情	详情

Extended Information