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【结 构 式】

【分子编号】45462

【品名】Methyl 3-(chlorosulfonyl)propanoate; 3-(Chlorosulfonyl)propionic acid methylester

【CA登记号】15441-07-3

【 分 子 式 】C4H7ClO4S

【 分 子 量 】186.61588

【元素组成】C 25.74% H 3.78% Cl 19% O 34.29% S 17.18%

与该中间体有关的原料药合成路线共 1 条

合成路线1

该中间体在本合成路线中的序号:(VII)

Condensation of 2-(4-methylphenyl)ethanol (I) with t-Bu-bromoacetate (II) in toluene in the presence of NaOH and tetrabutylammonium bromide (TBAB) provides ethoxyacetic acid derivative (III), which is converted into acetamide (V) by reaction with oxalyl chloride (IV) in toluene/DMF followed by treatment with NH4OH. Reduction of (V) by reaction with borane-tetrahydrofuran (BH3·THF) in THF yields ethanamine (VI), which is then coupled to chlorosulfonyl derivative (VII) in CH2Cl2 in the presence of TEA to afford compound (VIII). Reduction of the ester group of (VIII) by treatment with diisobutylaluminium hydride (DIBAL) in toluene furnishes aldehyde (IX), which is finally subjected to a reductive amination with benzothiazol derivative (X) by means of NaCNBH3 in MeOH/HOAc.

1 Bonnert, R.; et al.; The discovery of dual D2-receptor and beta2-adrenoceptor agonists for the treatment of airway diseases. 16th Int Symp Med Chem (Sept 18 2000, Bologna) 2000, Poster PC161.
2 Bonnert, R.V.; Brown, R.C.; Cage, P.A.; Ince, F.; Pairaudeau, G. (AstraZeneca plc); Benzothiazolone derivs.. JP 1999512422; US 5846989; WO 9710227 .
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) 45458 2-(4-methylphenyl)-1-ethanol 699-02-5 C9H12O 详情 详情
(II) 17430 2-Bromoacetic acid tert-butyl ester; tert-butyl 2-bromoacetate; tert-Butyl bromoacetate 5292-43-3 C6H11BrO2 详情 详情
(III) 45459 2-[(4-methylphenethyl)oxy]acetic acid C11H14O3 详情 详情
(IV) 29841 Oxalyl chloride; 2-Chloro-2-oxoacetyl chloride 79-37-8 C2Cl2O2 详情 详情
(V) 45460 2-[(4-methylphenethyl)oxy]acetamide C11H15NO2 详情 详情
(VI) 45461 2-[(4-methylphenethyl)oxy]ethylamine; 2-[(4-methylphenethyl)oxy]-1-ethanamine C11H17NO 详情 详情
(VII) 45462 Methyl 3-(chlorosulfonyl)propanoate; 3-(Chlorosulfonyl)propionic acid methylester 15441-07-3 C4H7ClO4S 详情 详情
(VIII) 45463 methyl 3-[([2-[(4-methylphenethyl)oxy]ethyl]amino)sulfonyl]propanoate C15H23NO5S 详情 详情
(IX) 45464 N-[2-[(4-methylphenethyl)oxy]ethyl]-3-oxo-1-propanesulfonamide C14H21NO4S 详情 详情
(X) 25944 7-(2-aminoethyl)-4-hydroxy-1,3-benzothiazol-2(3H)-one C9H10N2O2S 详情 详情
Extended Information