5-(chlorosulfonyl)-2-methoxybenzoic acid -Drug Synthesis Database

【结构式】

【分子编号】21354

【品名】5-(chlorosulfonyl)-2-methoxybenzoic acid

【CA登记号】

【分子式】C₈H₇ClO₅S

【分子量】250.65928

【元素组成】C 38.33% H 2.81% Cl 14.14% O 31.91% S 12.79%

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：(X)

This compound is obtained by condensation of 2(S)-(aminomethyl)-1-ethylpyrrolidine (I) with 5-(aminosulfonyl)-2-methoxybenzoyl chloride (II) by means of K2CO3 in acetone. The starting compounds (I) and (II) are obtained as follows: a) The acylation of 2(S)-(hydroxymethyl)pyrrolidine (III) with acetic anhydride in refluxing methanol gives 1-acetyl-2(S)-(hydroxymethyl)pyrrolidine (IV), which by reaction with SOCl2 in CHCl3 is converted into 1-acetyl-2(S)-(chloromethyl)pyrrolidine (V). The reaction of (V) with sodium azide in hot DMF affords the corresponding azide (VI), which is reduced with LiAlH4 in refluxing THF to yield the desired product (I). b) The methylation of 2-hydroxybenzaldehyde (VII) with dimethyl sulfate and K2SO3 in refluxing acetone gives 2-methoxybenzaldehyde (VIII), which is oxidized with KMnO4 in hot aqueous NaOH affording 2-methoxybenzoic acid (IX). The sulfonation of (IX) with hot chlorosulfonic acid yields 5-(chlorosulfonyl)-2-methoxybenzoic acid (X), which is finally treated with 28% aqueous NaOH to give the desired product (II).

参考文献中间体

合成目标

【1】 Al-Koutayni-Rifai, M.; Jamet, G.; Kerr, R.R.; Jung, L.; Koffel, J.C.; Synthesis of D3-sulpiride and its (R) and (S) isomers. J Label Compd Radiopharm 1989, 27, 7, 811.

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)	21345	(2S)-1-Ethyl-2-(aminomethyl)pyrrolidine; [(2S)-1-Ethylpyrrolidinyl]methanamine		C₇H₁₆N₂	详情	详情
(II)	21346	5-(aminosulfonyl)-2-methoxybenzoyl chloride		C₈H₈ClNO₄S	详情	详情
(III)	21347	(2S)pyrrolidinylmethanol	23356-96-9	C₅H₁₁NO	详情	详情
(IV)	21348	1-[(2S)-2-(hydroxymethyl)pyrrolidinyl]-1-ethanone		C₇H₁₃NO₂	详情	详情
(V)	21349	1-[(2S)-2-(chloromethyl)pyrrolidinyl]-1-ethanone		C₇H₁₂ClNO	详情	详情
(VI)	21350	1-[(2S)-2-(azidomethyl)pyrrolidinyl]-1-ethanone		C₇H₁₂N₄O	详情	详情
(VII)	21351	2-Hydroxybenzaldehyde;Salicylic aldehyde；2-Formylphenol;salicylaldehyde	90-02-8	C₇H₆O₂	详情	详情
(VIII)	12568	2-Methoxybenzaldehyde; o-Methoxybenzaldehyde	135-02-4	C₈H₈O₂	详情	详情
(IX)	13926	2-Methoxybenzoic acid; o-Methoxybenzoic Acid	579-75-9	C₈H₈O₃	详情	详情
(X)	21354	5-(chlorosulfonyl)-2-methoxybenzoic acid		C₈H₇ClO₅S	详情	详情
(XI)	21355	5-(aminosulfonyl)-2-methoxybenzoic acid; 2-methoxy-5-sulfamoylbenzoic acid	22117-85-7	C₈H₉NO₅S	详情	详情

合成路线2

该中间体在本合成路线中的序号：(I)

A new procedure for the synthesis of sulmepride has been reported: 5-chlorosulfonyl-2-methoxybenzoic acid (I) reacts with 2-(aminomethyl)-1-methylpyrrolidine (II) and thionyl chloride to give 5-chlorosulfonyl-N-[(1-methyl-2-pyrrolidinyl)methyl]-2-methoxybenzamide (III) which is treated with ammonia

参考文献中间体

合成目标

【1】 FR 2478093 .

中间体序号	中间体编号	品名	分子式	供应商	用于合成
(I)	21354	5-(chlorosulfonyl)-2-methoxybenzoic acid	C₈H₇ClO₅S	详情	详情
(II)	60759	(1-methyl-2-pyrrolidinyl)methylamine; (1-methyl-2-pyrrolidinyl)methanamine	C₆H₁₄N₂	详情	详情
(III)	60760	4-methoxy-3-({[(1-methyl-2-pyrrolidinyl)methyl]amino}carbonyl)benzenesulfonyl chloride	C₁₄H₁₉ClN₂O₄S	详情	详情

Extended Information