Hydrochloric Acid → L-Alanyl-L-Glutamine

HRID 1373731Notes

Reaction equation

HRID 1373731 reaction equation
ClC(Cl)(Cl)C(Cl)(Cl)Cl.C([NH:19][C@H:20]([C:22](O)=[O:23])[CH3:21])(OCC1C=CC=CC=1)=O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.O.[NH2:45][C@H:46]([C:52]([OH:54])=[O:53])[CH2:47][CH2:48][C:49](=[O:51])[NH2:50].[OH-].[Na+].C(=O)([O-])[O-].[K+].[K+].Cl>CCOCC.C(#N)C>[NH2:19][C@H:20]([C:22]([NH:45][C@H:46]([C:52]([OH:54])=[O:53])[CH2:47][CH2:48][C:49](=[O:51])[NH2:50])=[O:23])[CH3:21]

Participants

11

Reactant 8

HCID 313Hydrochloric AcidHCID 962WaterHCID 5961L-GlutamineHCID 6214HexachloroethaneHCID 11430Potassium CarbonateHCID 11776TriphenylphosphineHCID 14798Sodium HydroxideHCID 736104N-carbobenzyloxyalanine

Product 1

HCID 123935L-Alanyl-L-GlutamineYield 45%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6342AcetonitrileSolvent2×

Procedure

Dissolve 30 mmol of hexachloroethane with 10 ml of acetonitrile, drop it into a mixed system composed of 10 mmol of carbobenzoxy alanine (Z-Ala), 20 ml of triphenylphosphine and 10 ml of acetonitrile. After reacting at 5° C. for 1.0 h., drop it into 20 ml of water containing 10 mmol of glutamine. While reacting, regulate pH to 10 with 20 mmol of sodium hydroxide and then potassium carbonate successively, the reaction temperature is 5° C., and the reaction time after dropping is 2 hours. And then acidify it to regulate pH to 3.0 with concentrated hydrochloric acid. The aqueous phase, after concentrated, reacts with trifluoroacetic acid at room temperature for 40 hours. After the reaction is finished, add in 50 ml of ether, solids deposit, the product L-Ala-L-Gln is obtained with a yield of 45% by recrystallizing the solids with 1,4-dioxane-water.

Workup

  1. customis 5° C.
  2. waitthe reaction time after dropping is 2 hours
  3. concentrationThe aqueous phase, after concentrated
  4. customreacts with trifluoroacetic acid at room temperature for 40 hours

Sources & evidence

ORD record
ord-9d99489a8bb5469ea661edfba2a0c400
Source dataset
uspto-grants-2007_01
Patent number
US07163917B2

Reaction notes

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