Sulfuric Acid → L-Alanyl-L-Glutamine

HRID 1373724Notes

Reaction equation

HRID 1373724 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.ClC(Cl)(Cl)C(Cl)(Cl)Cl.[NH2:28][C@H:29]([C:35]([OH:37])=[O:36])[CH2:30][CH2:31][C:32](=[O:34])[NH2:33].[C:38](=[O:41])([O-])[O-].[Na+].[Na+].S(=O)(=O)(O)O.[C:49](#[N:51])[CH3:50]>CCOCC.C1(C)C=CC=CC=1.O>[NH2:51][C@H:49]([C:38]([NH:28][C@H:29]([C:35]([OH:37])=[O:36])[CH2:30][CH2:31][C:32](=[O:34])[NH2:33])=[O:41])[CH3:50]

Participants

10

Reactant 6

HCID 1118Sulfuric AcidHCID 5961L-GlutamineHCID 6214HexachloroethaneHCID 6342AcetonitrileHCID 10340Sodium CarbonateHCID 11776Triphenylphosphine

Product 1

HCID 123935L-Alanyl-L-GlutamineYield 40%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 1140TolueneSolventHCID 3283Diethyl EtherSolvent

Procedure

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.

Workup

  1. customis 30° C.
  2. waitthe reaction time after dropping is 1 hour
  3. concentrationThe aqueous phase, after concentrated
  4. customreacts with saturated hydrogen bromide/1,4-dioxane at room temperature for 5 hours

Sources & evidence

ORD record
ord-3d0f053bbeae427ca08057f4d58511c5
Source dataset
uspto-grants-2007_01
Patent number
US07163917B2

Reaction notes

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