* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
With chromium(VI) oxide; acetic anhydride In dichloromethane at 0 - 20℃;
Experimental Procedures-Part 1 :; Step 1 - Oxidation of Carboxymethylcyclopentene:; Procedure:; To a cooled (00C) 2 L round bottom flask with a magnetic stir bar and internal temperature probe was added acetic anhydride (615 g, 570 mL, 6.02 mol). Chromium trioxide (214 g, 2.14 mol) was added in portions while maintaining constant stirring and to control the exotherm. The resulting blood red solution was stirred to dissolve the chromium trioxide until the temperature had cooled to 20 0C. A 5 L three-neck flask was fitted with an addition funnel, overhead stirring mechanism, nitrogen inlet and internal temperature probe and charged with 4 (100 g, 101 mL, 0.793 mol) in 1.4 L CH2Cl2. The oxidizing solution of chromium trioxide and acetic anhydride was charged to the addition funnel and added dropwise to the reaction mixture, maintaining the internal temperature between 10 and 14 0C. The initially yellow solution became dark after the first few drops of oxidizer were added.The reaction was worked up in two equally-sized batches due to limitations on vessel size in the laboratory. Each batch was treated exactly the same way, as follows: The dark, homogeneous solution was poured carefully into a 4 L beaker with an overhead stirring mechanism. The reaction flask was rinsed with 250 mL CH2Cl2. 500 mL H2O was added followed by 10 g NaHCC"3 which resulted in gas evolution. Additional NaHCC>3 (830 g, 10 mol) was added in portions while maintaining 500 rpm stir rate in the viscous mixture. The resulting dark green suspension was diluted with 1 L H2O and filtered through a 3 L fritted funnel containing a 1 cm pad of solka floe. The biphasic solution was extracted with CH2CI2 (3x1 L) and the combined organics dried using MgSO.), then filtered and the resulting solution was concentrated in vacuo to afford a pale green oil. Distillation through a 30 cm Vigreux column followed by recrystallization from MTBE:hexane (1:10, 55 mL total) provided 38.4 g of 5 as a white crystalline solid (35percent).ted yield
Reference：
[1] Journal of the American Chemical Society, 2004, vol. 126, # 42, p. 13622 - 13623
[2] Organic and Biomolecular Chemistry, 2008, vol. 6, # 12, p. 2195 - 2203
[3] Green Chemistry, 2017, vol. 19, # 2, p. 511 - 518
[4] Patent: WO2008/21029, 2008, A2, . Location in patent: Page/Page column 39; 47
[5] Journal of Organometallic Chemistry, 2007, vol. 692, # 24, p. 5523 - 5527
[6] Tetrahedron, 1995, vol. 51, # 43, p. 11751 - 11764
[7] Green Chemistry, 2017, vol. 19, # 21, p. 5122 - 5130
[8] Journal of Medicinal Chemistry, 2017, vol. 60, # 21, p. 9022 - 9039
4
[ 75-91-2 ]
[ 25662-28-6 ]
[ 108384-35-6 ]
Reference：
[1] Journal of the American Chemical Society, 2003, vol. 125, # 11, p. 3232 - 3233
5
[ 162086-59-1 ]
[ 108384-35-6 ]
Reference：
[1] Green Chemistry, 2017, vol. 19, # 21, p. 5122 - 5130
With chromium(VI) oxide; acetic anhydride; In dichloromethane; at 0 - 20℃;
Experimental Procedures-Part 1 :; Step 1 - Oxidation of Carboxymethylcyclopentene:; Procedure:; To a cooled (00C) 2 L round bottom flask with a magnetic stir bar and internal temperature probe was added acetic anhydride (615 g, 570 mL, 6.02 mol). Chromium trioxide (214 g, 2.14 mol) was added in portions while maintaining constant stirring and to control the exotherm. The resulting blood red solution was stirred to dissolve the chromium trioxide until the temperature had cooled to 20 0C. A 5 L three-neck flask was fitted with an addition funnel, overhead stirring mechanism, nitrogen inlet and internal temperature probe and charged with 4 (100 g, 101 mL, 0.793 mol) in 1.4 L CH2Cl2. The oxidizing solution of chromium trioxide and acetic anhydride was charged to the addition funnel and added dropwise to the reaction mixture, maintaining the internal temperature between 10 and 14 0C. The initially yellow solution became dark after the first few drops of oxidizer were added.The reaction was worked up in two equally-sized batches due to limitations on vessel size in the laboratory. Each batch was treated exactly the same way, as follows: The dark, homogeneous solution was poured carefully into a 4 L beaker with an overhead stirring mechanism. The reaction flask was rinsed with 250 mL CH2Cl2. 500 mL H2O was added followed by 10 g NaHCC«3 which resulted in gas evolution. Additional NaHCC>3 (830 g, 10 mol) was added in portions while maintaining 500 rpm stir rate in the viscous mixture. The resulting dark green suspension was diluted with 1 L H2O and filtered through a 3 L fritted funnel containing a 1 cm pad of solka floe. The biphasic solution was extracted with CH2CI2 (3x1 L) and the combined organics dried using MgSO.), then filtered and the resulting solution was concentrated in vacuo to afford a pale green oil. Distillation through a 30 cm Vigreux column followed by recrystallization from MTBE:hexane (1:10, 55 mL total) provided 38.4 g of 5 as a white crystalline solid (35%).ted yield
With sulfuric acid; sodium formate; nicotinamide adenine dinucleotide;formate dehydrogenase; alcohol dehydrogenase RE; In water; at 25℃; for 24h;pH 6.5 - 7;potassium dibasic buffer; Enzymatic reaction;
Formate dehydrogenase; Procedure:; To potassium dibasic buffer (100 mM, pH 7.0, 2 L), sodium formate (120 g) and nicotinamide adenine dinucleotide (NAD, 8 gram) was added which reduced the buffer pH to 6.7. The enzymes were added to the buffer: alcohol dehydrogenase RE (5 g, 185 KU)3 formate dehydrogenase (20 g, 94 KU). Substrate 5 (1O g, 0.071 mol) was added directly as a powder and the temperature controlled at 25 0C with the pH controlled at 6.5 using 2N sulphuric acid. Reaction was aged for 24 hours then extracted with ethyl acetate (2 volume extractions) followed by vacuum concentration. Overall yield of 6 was 83% with 2% loss from extraction and < 3% residual enone. The remaining 13% mass balance was determined to be enone loss from instability in aqueous.
Chemistry
Pharmaceutical Intermediates
Inhibitors/Agonists
Material Science
For Research Only
110K+ Compounds
Competitive Price
1-2 Day Shipping
