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Chemical Structure| 21066-72-8 Chemical Structure| 21066-72-8

Structure of 21066-72-8

Chemical Structure| 21066-72-8

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Product Details of [ 21066-72-8 ]

CAS No. :21066-72-8
Formula : C8H14O6
M.W : 206.19
SMILES Code : CCOC([C@@H]([C@@H](C(OCC)=O)O)O)=O

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Application In Synthesis of [ 21066-72-8 ]

* 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.

  • Downstream synthetic route of [ 21066-72-8 ]

[ 21066-72-8 ] Synthesis Path-Downstream   1~1

  • 1
  • [ 21066-72-8 ]
  • [ 73590-85-9 ]
  • esomeprazole potassium [ No CAS ]
YieldReaction ConditionsOperation in experiment
74% Water (157.6 mul) was added to a solution of 5-methoxy-2-[[(4-methoxy-3,5-dimethyl-2-pyridinyl)methyl]thio]-1H-benzimidazole in toluene (370 ml; 211.5 g/l) with a water content 25 of 0.031percent (w/w), followed by addition of D-(-)-diethyl tartrate (8.55 ml). The solution was heated to 50° C. and stirred at this temperature for 20 minutes. Titanium (IV) isopropoxide (7.15 ml) was added and reaction was left at 50° C. for 45 minutes. The temperature was lowered to 30° C. and diisopropylethylamine (6.2 ml) was added. Cumene hydroperoxide was added at an appropriate speed to maintain the temperature from 28° C. to 34° C. The temperature was raised to 35° C. after 2 hours and potassium methoxide (24.55 g) in methanol (222 ml) was added. The mixture was filtered after 14 hours and the crystals were washed with methanol:toluene (240 ml; 1:1) and methanol (120 ml) and dried. Yield: 79 g (74percent), ee>99.9percent. [00044] [alpha]D20=+28.7° (c=1percent, water); Assay: 89percent is S-5-methoxy-2-[[(4-methoxy-3,5-dimethyl-2-pyridinyl)-methyl]sulfinyl]-1H-benzimidazole potassium salt (11percent is methanol). [00045] 1H-NMR (200 MHz, DMSO-d6, delta ppm): 2.23 (s, 3H), 2.24 (s, 3H), 3.71 (s, 3H), 3.75 (s, 3H), 4.40 (d, 1H), 4.78 (d, 1H), 6.58 (dd, 1H), 7.00 (d, 1H), 7.35 (d, 1H), 8.25 (s, 1H).
54% Example 2 S-5-methoxy-2-[[(4-methoxy-3,5-dimethyl-2-pyridinyl)methyl]sulfnyl]-1H-benzimidazole Potassium Salt A solution of 5-methoxy-2-[[(4-methoxy-3,5-dimethyl-2-pyridinyl)methyl]thio]-1H-benzimidazole (15.4 g, 46.8 mmol) in toluene (70 ml) was heated to 50° C. and water (0.05 ml, 2.8 mmol) and D-(-)-diethyl tartrate (2.02 g, 9.82 mmol) were added.. The reaction mixture was stirred for 20 minutes.. titanium (IV) isopropoxide (1.34 g, 4.68 mmol) was added and the reaction mixture was stirred for 45 minutes.. The mixture was cooled to 30° C. and diisopropylethylamine (0.91 g, 7.01 mmol) was added followed by cumene hydroperoxide (9.52 g, 51.89 mmol).. The resultant mixture was stirred at 30° C. for 3 hours.. methanol (40 ml) was added followed by potassium hydroxide (3.05 g, 46.8 mmol) in methanol (30 ml).. Seed crystals were added and the reaction mixture was stirred at 35° C. overnight.. The precipitated product was filtered off, washed with methanol and toluene and dried in vacuo. Yield: 9.74 g (54percent).
 

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