【结 构 式】 |
【分子编号】21346 【品名】5-(aminosulfonyl)-2-methoxybenzoyl chloride 【CA登记号】 |
【 分 子 式 】C8H8ClNO4S 【 分 子 量 】249.67456 【元素组成】C 38.49% H 3.23% Cl 14.2% N 5.61% O 25.63% S 12.84% |
合成路线1
该中间体在本合成路线中的序号:(II)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).
【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 |