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Помогите пожалуйста с поиском методик синтеза следующего соединения:
CAS 72-14-0
SMILES: Nc1ccc(S(=O)(=O)Nc2nccs2)cc1
InChI Key JNMRHUJNCSQMMB-UHFFFAOYSA-N
Заранее спасибо
+++Поиск по Реаксис
+++Поиск по Реаксис
Последний раз редактировалось baja2007b Вс мар 01, 2026 8:40 pm, всего редактировалось 1 раз.
Re: Поиск по Реаксис
есть только получение такого замещенного
(R)-4-(3-hydroxy-2-oxopyrrolidin-1-yl)-N-(thiazol-2-yl)benzenesulfonamide
Stage #1: (R)-4-(3-(tert-butyldiphenylsilyloxy)-2-oxopyrrolidin-1-yl)-N-(thiazol-2-yl)benzenesulfonamide With tetrabutyl ammonium fluoride In tetrahydrofuran at 20℃;
Stage #2: With water In tetrahydrofuran
Experimental Procedure
76%
Current Patent Assignee: VERTEX PHARMACEUTICALS - US2009/124655, 2009, A1
Location in patent: Page/Page column 19-20
Experimental Procedure
To a solution of (R)-4-(3-(tert-butyldiphenylsilyloxy)-2-oxopyrrolidin-1-yl-N-(thiazol-2-yl)benzenesulfonamide (5.5 g, 9.53 mmol) in THF (40 mL) under N2, was added a solution of tetrabutyl ammonium fluoride in THF (1M, 40 mL, 38.12 mmol). Upon completion of addition, the mixture was stirred at RT overnight. The reaction mixture was poured into water and extracted with CH2Cl2 (2*50 mL), dried over magnesium sulfate, and concentrated. Purification via silica gel chromatography using 2-10% MeOH in CH2Cl2 gave (R)-4-(3-hydroxy-2-oxopyrrolidin-1-yl-N-(thiazol-2-yl)benzenesulfonamide (2.6 g, 76%). LC/MS (10%-99% CH3CN (0.035% TFA)/H2O (0.05% TFA)), m/z: M+1 obs=340.0; tR=0.54 min.
(R)-4-(3-hydroxy-2-oxopyrrolidin-1-yl)-N-(thiazol-2-yl)benzenesulfonamide
Stage #1: (R)-4-(3-(tert-butyldiphenylsilyloxy)-2-oxopyrrolidin-1-yl)-N-(thiazol-2-yl)benzenesulfonamide With tetrabutyl ammonium fluoride In tetrahydrofuran at 20℃;
Stage #2: With water In tetrahydrofuran
Experimental Procedure
76%
Current Patent Assignee: VERTEX PHARMACEUTICALS - US2009/124655, 2009, A1
Location in patent: Page/Page column 19-20
Experimental Procedure
To a solution of (R)-4-(3-(tert-butyldiphenylsilyloxy)-2-oxopyrrolidin-1-yl-N-(thiazol-2-yl)benzenesulfonamide (5.5 g, 9.53 mmol) in THF (40 mL) under N2, was added a solution of tetrabutyl ammonium fluoride in THF (1M, 40 mL, 38.12 mmol). Upon completion of addition, the mixture was stirred at RT overnight. The reaction mixture was poured into water and extracted with CH2Cl2 (2*50 mL), dried over magnesium sulfate, and concentrated. Purification via silica gel chromatography using 2-10% MeOH in CH2Cl2 gave (R)-4-(3-hydroxy-2-oxopyrrolidin-1-yl-N-(thiazol-2-yl)benzenesulfonamide (2.6 g, 76%). LC/MS (10%-99% CH3CN (0.035% TFA)/H2O (0.05% TFA)), m/z: M+1 obs=340.0; tR=0.54 min.
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