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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1373724Generated: November 2, 2026

Sulfuric Acid → L-Alanyl-L-Glutamine

https://huagongshe.com/reaction/1373724

Reaction equation

Participants

RoleNameHCIDCharge
ReactantSulfuric AcidHCID 1118—
ReactantL-GlutamineHCID 5961—
ReactantHexachloroethaneHCID 6214—
ReactantAcetonitrileHCID 6342—
ReactantSodium CarbonateHCID 10340—
ReactantTriphenylphosphineHCID 11776—
SolventWaterHCID 962—
SolventTolueneHCID 1140—
SolventDiethyl EtherHCID 3283—
ProductL-Alanyl-L-GlutamineHCID 12393540%

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

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS07163917B2
Source datasetuspto-grants-2007_01
ORD IDord-3d0f053bbeae427ca08057f4d58511c5
Source noteuspto-grants-2007_01