Nitric Acid → L-Alanyl-L-Glutamine

HRID 1373723Notes

Reaction equation

HRID 1373723 reaction equation
[C:1]1(P(C2C=CC=CC=2)C2C=CC=CC=2)[CH:6]=CC=C[CH:2]=1.[NH2:20][C@H:21]([C:27]([OH:29])=[O:28])[CH2:22][CH2:23][C:24](=[O:26])[NH2:25].[OH-:30].[K+].[N+:32]([O-])(O)=O>CCOCC.C1CCCCC1.O.ClCCl>[NH2:32][C@H:1]([C:6]([NH:20][C@H:21]([C:27]([OH:29])=[O:28])[CH2:22][CH2:23][C:24](=[O:26])[NH2:25])=[O:30])[CH3:2]

Participants

9

Reactant 4

HCID 944Nitric AcidHCID 5961L-GlutamineHCID 11776TriphenylphosphineHCID 14797Potassium Hydroxide

Product 1

HCID 123935L-Alanyl-L-GlutamineYield 60%

Reagents, catalysts & solvents 4

HCID 962WaterSolventHCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent2×HCID 8078CyclohexaneSolvent

Procedure

Dissolve 30 mmol of hexaethane with 20 ml of dichloromethane, drop it into a mixed system composed of 10 mmol of N—(O,O-diethyl) phosphoalanine, 30 mmol of triphenylphosphine and 10 ml of dichloromethane. After reacting at 0° C. for 40 min., drop it into a liquid mixture containing 30 mmol of glutamine, 20 ml of water and 10 ml of cyclohexane. While reacting, regulate pH to 13 with potassium hydroxide, the reaction temperature is 20° C., the reaction time after dropping is 30 min. And then acidify it to regulate pH=1.5 with dilute nitric acid. The aqueous phase, after concentrated, react with trifluoroacetic acid at room temperature for 10 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 60% by recrystallizing the solids with 1,4-dioxane-water.

Workup

  1. customis 20° C.
  2. waitthe reaction time after dropping is 30 min
  3. concentrationThe aqueous phase, after concentrated
  4. customreact with trifluoroacetic acid at room temperature for 10 hours

Sources & evidence

ORD record
ord-e2e6494bbe0c464280d2bf46bf9a6735
Source dataset
uspto-grants-2007_01
Patent number
US07163917B2

Reaction notes

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