(S)-3,4-二氢-4-羟基-2-(3-甲氧丙基)-2H-噻吩并[3,2-E]-1,2-噻嗪-6-磺酰胺 1,1-二氧化物合成路线 （共 8 条）
反应条件
1: With (−)-DIP-Chloride™ in hexane; tert-butyl methyl ether T=-40 - -20°C; Inert atmosphere; 2: With sodium hydroxide in hexane; tert-butyl methyl ether; water T=25 - 30°C;
参考文献
AZAD PHARMACEUTICAL INGREDIENTS AG; RAMAKRISHNAN, Arul; SONI, Anil Kumar; ADHIKARI, Sujit Das; RAO, Kommula Srinivasa; PAUL, Soumendu; SRINIVASULU, Ganta
Patent: WO2010/103115 A1, 2010 ;
Location in patent: Page/Page column 15-16 ;
反应条件
1: With sec.-butyllithium in tetrahydrofuran; cyclohexane T=-5 - 0°C; 8.75 h; Inert atmosphere; 2: With sulfur dioxide in tetrahydrofuran; cyclohexane T=-65 - 20°C; Inert atmosphere; 3: With NaOAc·3H2O; hydroxylamine-o-sulphonic acid in water T=0 - 20°C; Product distribution / selectivity;
参考文献
Sathe, Dhananjay Govind; Tarur, Radhakrishnan Venkatasubramanian; Bhise, Nandu Baban; Shinde, Ajit Bhaskar; Pardeshi, Santosh
Patent: US2010/9977 A1, 2010 ;
Location in patent: Page/Page column 11 ;
反应条件
1: With n-butyllithium in tetrahydrofuran; hexane T=-70 - -66°C; 3.5 h; Inert atmosphere; 2: With sulfur dioxide in tetrahydrofuran; hexane T=20°C; pH=4; 3: With NaOAc·3H2O; hydroxylamine-o-sulphonic acid in water T=0 - 25°C; 15 h;
参考文献
Conrow, Raymond E.; Dean, W. Dennis; Zinke, Paul W.; Deason, Michael E.; Sproull, Steven J.; Dantanarayana, Anura P.; DuPriest, Mark T.
Organic Process Research and Development, 1999 , vol. 3, # 2 p. 114 - 120
参考文献
Alcon Laboratories, Inc.
Patent: US5378703 A1, 1995 ;
反应条件
1.1: thiourea / ethanol; water / 2 h / |Reflux; |Large scale 1.2: 3 h / |Reflux; |Large scale 2.1: chlorine / toluene / 0.42 h / 8 °C / |Cooling with ice 3.1: ammonia / 1 h / 5 - 15 °C 4.1: Na2WO4·2H2O; dihydrogen peroxide / water / 19 h / 15 - 35 °C 5.1: pyridinium tribromide; sulfuric acid / ethyl acetate / 1.5 h / 1 - 5 °C / |Large scale 6.1: bis[(1S,2R,3S,5S)-pinan-3-yl]chloroborane / tert-butyl methyl ether / 3.5 h / -40 - -32 °C / |Inert atmosphere 6.2: 2 h / 0 - 22 °C 7.1: potassium carbonate / dimethyl sulfoxide 8.1: n-butyllithium / hexane; tetrahydrofuran / 3.5 h / -70 - -66 °C / |Inert atmosphere 8.2: 20 °C / pH 4 8.3: 15 h / 0 - 25 °C View Scheme
参考文献
Organic Process Research and Development, , vol. 3, # 2 p. 114 - 120
反应条件
1.1: chlorine / toluene / 0.42 h / 8 °C / |Cooling with ice 2.1: ammonia / 1 h / 5 - 15 °C 3.1: Na2WO4·2H2O; dihydrogen peroxide / water / 19 h / 15 - 35 °C 4.1: pyridinium tribromide; sulfuric acid / ethyl acetate / 1.5 h / 1 - 5 °C / |Large scale 5.1: bis[(1S,2R,3S,5S)-pinan-3-yl]chloroborane / tert-butyl methyl ether / 3.5 h / -40 - -32 °C / |Inert atmosphere 5.2: 2 h / 0 - 22 °C 6.1: potassium carbonate / dimethyl sulfoxide 7.1: n-butyllithium / hexane; tetrahydrofuran / 3.5 h / -70 - -66 °C / |Inert atmosphere 7.2: 20 °C / pH 4 7.3: 15 h / 0 - 25 °C View Scheme
参考文献
Organic Process Research and Development, , vol. 3, # 2 p. 114 - 120
反应条件
1: (S)-3,4-dihydro-4-hydroxy-2(3-methoxypropyl)-4H-thieno[3,2-e]-1,2-thiazine-6-sulfonamide-1,1-dioxide With toluene-4-sulfonic acid; triethylamine in tetrahydrofuran T=0 - 20°C; 18 h; 2: ethylamine in tetrahydrofuran T=0 - 20°C; 36 h;
参考文献
Sathe, Dhananjay Govind; Tarur, Radhakrishnan Venkatasubramanian; Bhise, Nandu Baban; Shinde, Ajit Bhaskar; Pardeshi, Santosh
Patent: US2010/9977 A1, 2010 ;
Location in patent: Page/Page column 11-12 ;
反应条件
1: acetonitrile / 19 h / 30 - 85 °C / |Reflux 2: triethylamine / tetrahydrofuran / 2 h / -10 - -2 °C / |Inert atmosphere 3: water / 15 h / 11 - 20 °C View Scheme
参考文献
Conrow, Raymond E.; Dean, W. Dennis; Zinke, Paul W.; Deason, Michael E.; Sproull, Steven J.; Dantanarayana, Anura P.; DuPriest, Mark T.
Organic Process Research and Development, 1999 , vol. 3, # 2 p. 114 - 120
