Alternatived Products of [ 118380-06-6 ]
Product Details of [ 118380-06-6 ]
| CAS No. : | 118380-06-6 |
MDL No. : | MFCD01863426 |
| Formula : |
C11H15NO6
|
Boiling Point : |
- |
| Linear Structure Formula : | - |
InChI Key : | - |
| M.W : |
257.24
|
Pubchem ID : | - |
| Synonyms : |
|
Safety of [ 118380-06-6 ]
| Signal Word: | |
Class: | |
| Precautionary Statements: | |
UN#: | |
| Hazard Statements: | |
Packing Group: | |
Application In Synthesis of [ 118380-06-6 ]
* 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 [ 118380-06-6 ]
- 1
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[ 6066-82-6 ]
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[ 627-91-8 ]
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[ 118380-06-6 ]
| Yield | Reaction Conditions | Operation in experiment |
|
With triethylamine; In thionyl chloride; dichloromethane; |
15 A solution of <strong>[627-91-8]adipic acid monomethyl ester</strong> (5.4 g, 33.3 mmol) in thionyl chloride (15 ml) was heated at 40 degrees C. for 2 hours. The mixture was then concentrated and distilled in vacuo (boiling point 119 degrees C. at 20 mm Hg) to provide 3.58 g (60 percent yield by weight) of the acid chloride methyl ester. This was dissolved in 20 ml of dichloromethane and N-hydroxysuccinimide (2.75 g, 24.0 mmol) was added, followed by triethylamine (4.2 ml, 30 mmol). The mixture stirred for 10 minutes then diluted with ethyl acetate and washed with 0.5 M HCL and brine. The solution was dried over anhydrous magnesium sulfate, filtered and concentrated to give 4.5 g (87.5 percent yield by weight) of methyl succinimidyl adipate) as a colorless oil. Proton NMR (in CDCl3): delta 3.73 (singlet, 3H); delta 2.90 (singlet 4H), delta 2.70 (multiplet, 2H), delta 2.37 (multiplet, 2H), and delta 1 79 (multiplet 4H). |
Reference：
[1]Journal of Medicinal Chemistry,1995,vol. 38,p. 1538 - 1546
[2]Chemical Research in Toxicology,1996,vol. 9,p. 466 - 475
[3]Bioorganic and Medicinal Chemistry Letters,2004,vol. 14,p. 4333 - 4338
[4]Patent: US5030717,1991,A
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[ 6066-82-6 ]
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[ 627-91-8 ]
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[ 111-50-2 ]
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[ 118380-06-6 ]
| Yield | Reaction Conditions | Operation in experiment |
| 87.5% |
With triethylamine; In thionyl chloride; dichloromethane; |
Adipoyl Chloride (Linking Agent) A solution of <strong>[627-91-8]adipic acid monomethyl ester</strong> (5.4 g, 33.3 mmol) in thionyl chloride (15 ml) was heated at 40 degrees C. for 2 hours. The mixture was then concentrated and distilled in vacuo (boiling point 119 degrees C. at 20 mm Hg) to provide 3.58 g (60 percent yield by weight) of the acid chloride methyl ester. This was dissolved in 20 ml of dichloromethane and N-hydroxysuccinimide (2.75 g, 24.0 mmol) was added, followed by triethylamine (4.2 ml, 30 mmol). The mixture stirred for 10 minutes then diluted with ethyl acetate and washed with 0.5 M HCL and brine. The solution was dried over anhydrous magnesium sulfate, filtered and concentrated to give 4.5 g (87.5 percent yield by weight) of methyl succinimidyl adipate) as a colorless oil. Proton NMR (in CDCl3): delta 3.73 (singlet, 3H; delta 2.90 (singlet 4H), delta 2.70 |
| 87.5% |
With triethylamine; In thionyl chloride; dichloromethane; |
Adipoyl Chloride (Linking Agent) A solution of <strong>[627-91-8]adipic acid monomethyl ester</strong> (5.4 g, 33.3 mmol) in thionyl chloride (15 ml) was heated at 40 degrees C. for 2 hours. The mixture was then concentrated and distilled in vacuo (boiling point 119 degrees C. at 20 mm Hg) to provide 3.58 g (60 percent yield by weight) of the acid chloride methyl ester. This was dissolved in 20 ml of dichloromethane and N-hydroxysuccinimide (2.75 g, 24.0 mmol) was added, followed by triethylamine (4.2 ml, 30 mmol). The mixture stirred for 10 minutes then diluted with ethyl acetate and washed with 0.5 M HCl and brine. The solution was dried over anhydrous magnesium sulfate, filtered and concentrated to give 4.5 g (87.5 percent yield by weight) of methyl succinimidyl adipate as a colorless oil. Proton NMR (in CDCl3) delta 3.73 (singlet, 3H); delta 2.90 (singlet 4H), delta 2.70 (multiplet, 2H), delta 2.37 (multiplet, 2H), and delta 1.79 (multiplet 4H). |
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