Sulfuric Acid → L-Alanyl-L-Glutamine

HRID 1373730Notes

Reaction equation

HRID 1373730 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C([NH:30][C@H:31]([C:33](O)=[O:34])[CH3:32])(OCC1C=CC=CC=1)=O.ClC(Cl)(Cl)C(Cl)(Cl)Cl.[NH2:44][C@H:45]([C:51]([OH:53])=[O:52])[CH2:46][CH2:47][C:48](=[O:50])[NH2:49].[OH-].[K+].S(=O)(=O)(O)O>ClCCl.O.O1CCCC1>[NH2:30][C@H:31]([C:33]([NH:44][C@H:45]([C:51]([OH:53])=[O:52])[CH2:46][CH2:47][C:48](=[O:50])[NH2:49])=[O:34])[CH3:32]

Participants

10

Reactant 6

HCID 1118Sulfuric AcidHCID 5961L-GlutamineHCID 6214HexachloroethaneHCID 11776TriphenylphosphineHCID 14797Potassium HydroxideHCID 736104N-carbobenzyloxyalanine

Product 1

HCID 123935L-Alanyl-L-GlutamineYield 65%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

Dissolve 15 mmol of triphenylphosphine with 10 ml of tetrahydrofuran, drop it into a mixed system composed of 10 mmol of carbobenzoxy-alanine (Z-Ala), 20 mmol of hexachloroethane and 10 ml of tetrahydrofuran. After reacting at 0° C. for 1.5 hours, drop it into a liquid mixture containing 18 mmol of glutamine, 20 ml of water and 40 ml of dichloromethane. While reacting, regulate pH to 13 with potassium hydroxide, the reaction temperature is 0° C., the reaction time after dropping is 2 hours. And then acidify it to regulate pH=2.0 with dilute sulfuric acid. The aqueous phase, after concentrated, reacts with hydrogen in methanol at room temperature for 15 hours. The product L-Ala-L-Gln with a yield of 65% is obtained.

Workup

  1. customis 0° C.
  2. waitthe reaction time after dropping is 2 hours
  3. concentrationThe aqueous phase, after concentrated
  4. customreacts with hydrogen in methanol at room temperature for 15 hours

Sources & evidence

ORD record
ord-f0a19682ec914754a6e48e6ddbbb7310
Source dataset
uspto-grants-2007_01
Patent number
US07163917B2

Reaction notes

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