Hydrochloric Acid → L-Alanyl-L-Glutamine

HRID 1373728Notes

Reaction equation

HRID 1373728 reaction equation
ClC(Cl)(Cl)C(Cl)(Cl)Cl.[NH:9](C(OC(C)(C)C)=O)[C@H:10]([C:12](O)=[O:13])[CH3:11].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[NH2:41][C@H:42]([C:48]([OH:50])=[O:49])[CH2:43][CH2:44][C:45](=[O:47])[NH2:46].[OH-].[K+].C(=O)([O-])[O-].[Na+].[Na+].Cl>CCOCC.ClCCl.O.O1CCCC1>[NH2:9][C@H:10]([C:12]([NH:41][C@H:42]([C:48]([OH:50])=[O:49])[CH2:43][CH2:44][C:45](=[O:47])[NH2:46])=[O:13])[CH3:11]

Participants

12

Reactant 7

HCID 313Hydrochloric AcidHCID 5961L-GlutamineHCID 6214HexachloroethaneHCID 10340Sodium CarbonateHCID 11776TriphenylphosphineHCID 14797Potassium HydroxideHCID 85082Tert-butoxycarbonylalanine

Product 1

HCID 123935L-Alanyl-L-GlutamineYield 45%

Reagents, catalysts & solvents 4

HCID 962WaterSolventHCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

Dissolve 20 mmol of hexachloroethane with 10 ml of tetrahydrofuran, drop it into a mixed system composed of 10 mmol of tert-butylcarbonylalnine (Boc-Ala), 20 mmol of triphenylphosphine and 20 ml of tetrahydrofuran. After reacting at 0° C. for 1.5 hours, drop it into a liquid mixture containing 20 mmol of glutamine, 20 ml of water and 15 ml of dichloromethane. While reacting, regulate pH to 10 with 20 mmol of potassium hydroxide and then with sodium carbonate successively, the reaction temperature is 8° C., the reaction time after dropping is 2 hours. And then acidify it to regulate pH=2.0 with concentrated hydrochloric acid. The aqueous phase, after concentrated, reacts with methylsulfonic acid at room temperature for 20 hours. As the reaction is finished, add in 50 ml of ether, solids deposit, the product L-Ala-L-Gln with a yield of 45% is obtained by recrystallizing the solids with methanol-water.

Workup

  1. customis 8° C.
  2. waitthe reaction time after dropping is 2 hours
  3. concentrationThe aqueous phase, after concentrated
  4. customreacts with methylsulfonic acid at room temperature for 20 hours

Sources & evidence

ORD record
ord-1065a09d6da047e0a11f8c75b3382029
Source dataset
uspto-grants-2007_01
Patent number
US07163917B2

Reaction notes

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