Nitric Acid → L-Alanyl-L-Glutamine

HRID 1373725Notes

Reaction equation

HRID 1373725 reaction equation
ClC(Cl)(Cl)C(Cl)(Cl)Cl.[C:9]1(P(C2C=CC=CC=2)C2C=CC=CC=2)[CH:14]=CC=C[CH:10]=1.[OH2:28].[NH2:29][C@H:30]([C:36]([OH:38])=[O:37])[CH2:31][CH2:32][C:33](=O)[NH2:34].[OH-:39].[K+].[N+:41]([O-])(O)=O>CCOCC.ClCCCl>[NH2:41][C@H:9]([C:14]([NH:29][C@H:30]([C:36]([OH:38])=[O:37])[CH2:31][CH2:32][C:33](=[O:39])[NH2:34])=[O:28])[CH3:10]

Participants

9

Reactant 6

HCID 944Nitric AcidHCID 962WaterHCID 5961L-GlutamineHCID 6214HexachloroethaneHCID 11776TriphenylphosphineHCID 14797Potassium Hydroxide

Product 1

HCID 123935L-Alanyl-L-GlutamineYield 52%

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolvent2×HCID 3283Diethyl EtherSolvent

Procedure

Dissolve 15 mmol of hexachloroethane with 10 ml of 1,2-dichloroethane, add it into a mixed system composed of 10 mmol of N—(O,O-diisopropyl) phosphoalanine, 15 mmol of triphenylphosphine, and 10 ml of 1,2-dichloroethane. After reacting at 20° C. for 1.5 hours, drop it into 20 ml of water containing 20 mmol of glutamine. While reacting, regulate pH to 13 with potassium hydroxide, the reaction temperature is 10° C., the reaction time after dropping is 2 hours. And then regulate pH to 1.5 by acidifying it with dilute nitric acid. The Aqueous phase, after concentrated, reacts 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 with a yield of 52% is obtained by recrystallizing the solids with isopropanol-water.

Workup

  1. additionadd it into a mixed system
  2. customis 10° C.
  3. waitthe reaction time after dropping is 2 hours
  4. concentrationThe Aqueous phase, after concentrated
  5. customreacts with trifluoroacetic acid at room temperature for 10 hours

Sources & evidence

ORD record
ord-d85b5c83892244bf9ca6a63530da9d4d
Source dataset
uspto-grants-2007_01
Patent number
US07163917B2

Reaction notes

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