Nitric Acid → L-Alanyl-L-Glutamine

HRID 1373726Notes

Reaction equation

HRID 1373726 reaction equation
C(C([NH:7][C@H:8]([C:10](O)=[O:11])[CH3:9])=O)(C)(C)C.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.ClC(Cl)(Cl)C(Cl)(Cl)Cl.[NH2:40][C@H:41]([C:47]([OH:49])=[O:48])[CH2:42][CH2:43][C:44](=[O:46])[NH2:45].[OH-].[K+].[N+]([O-])(O)=O>ClCCCl.CCOCC.C1CCCCC1.O>[NH2:7][C@H:8]([C:10]([NH:40][C@H:41]([C:47]([OH:49])=[O:48])[CH2:42][CH2:43][C:44](=[O:46])[NH2:45])=[O:11])[CH3:9]

Participants

11

Reactant 6

HCID 944Nitric AcidHCID 5961L-GlutamineHCID 6214HexachloroethaneHCID 11776TriphenylphosphineHCID 14797Potassium HydroxideHCID 42254381(S)-N-tert-butylcarbonylalanine

Product 1

HCID 123935L-Alanyl-L-GlutamineYield 40%

Reagents, catalysts & solvents 4

HCID 111,2-DichloroethaneSolventHCID 962WaterSolventHCID 3283Diethyl EtherSolventHCID 8078CyclohexaneSolvent

Procedure

In a round bottom flask, add in 10 mmol of tert-butylcarbonylalanine (Boc-Ala), 15 mmol of triphenyl phosphine and 20 mmol of hexachloroethane, and then add in 20 ml of 1,2-dichloroethane. After reacting at 10° C. for 20 min, drop it into a liquid mixture containing 30 mmol glutamine, 20 ml of water and 20 ml of cyclohexane. While reacting, regulate pH to 11 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, reacts with trifluoroacetic acid at room temperature for 15 hours. As the reaction is finished, add in 50 ml of ether, solids deposit, the product L-Ala-L-Gln with a yield of 40% is obtained by recrystallizing the solids with tetrahydrofuran-water.

Workup

  1. customis 20° C.
  2. waitthe reaction time after dropping is 30 min
  3. concentrationThe aqueous phase, after concentrated
  4. customreacts with trifluoroacetic acid at room temperature for 15 hours

Sources & evidence

ORD record
ord-fd5f25d28fb44971983842af9cd27cd5
Source dataset
uspto-grants-2007_01
Patent number
US07163917B2

Reaction notes

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