Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Sulfuric Acid | HCID 1118 | — |
| Reactant | L-Glutamine | HCID 5961 | — |
| Reactant | Hexachloroethane | HCID 6214 | — |
| Reactant | Acetonitrile | HCID 6342 | — |
| Reactant | Sodium Carbonate | HCID 10340 | — |
| Reactant | Triphenylphosphine | HCID 11776 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Toluene | HCID 1140 | — |
| Solvent | Diethyl Ether | HCID 3283 | — |
| Product | L-Alanyl-L-Glutamine | HCID 123935 | 40% |
Reaction Steps
In a round bottom flask, add in 10 mmol of N—(O,O-diethyl) phosphoalanine, 10 mmol of triphenylphosphine and 15 mmol of hexachloroethane respectively, and then add in 20 ml of acetonitrile. After reacting at 15° C. for 2.5 hour, drop it into a liquid mixture composed of 30 mmol of glutamine, 20 ml of water and 30 ml of toluene. While reacting, regulate pH to 8.5 with sodium carbonate, the reaction temperature is 30° C., the reaction time after dropping is 1 hour. And then acidify it to regulate pH=2 with dilute sulfuric acid. The aqueous phase, after concentrated, reacts with saturated hydrogen bromide/1,4-dioxane at room temperature for 5 hours. As the reaction is finished, add in 50 ml of ether, solids deposit, the product L-Ala-L-Gln is obtained with a yield of 40% by recrystallizing the solids with tetrahydrofuran-water.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US07163917B2 |
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| Source dataset | uspto-grants-2007_01 |
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| ORD ID | ord-3d0f053bbeae427ca08057f4d58511c5 |
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| Source note | uspto-grants-2007_01 |
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