Sulfuric Acid → L-Alanyl-L-Glutamine

HRID 1373727Notes

Reaction equation

HRID 1373727 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(C([NH:26][C@H:27]([C:29](O)=[O:30])[CH3:28])=O)(C)(C)C.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-].[Na+].S(=O)(=O)(O)O>CCOCC.O.C1(C)C=CC=CC=1>[NH2:26][C@H:27]([C:29]([NH:40][C@H:41]([C:47]([OH:49])=[O:48])[CH2:42][CH2:43][C:44](=[O:46])[NH2:45])=[O:30])[CH3:28]

Participants

10

Reactant 6

HCID 1118Sulfuric AcidHCID 5961L-GlutamineHCID 6214HexachloroethaneHCID 11776TriphenylphosphineHCID 14798Sodium HydroxideHCID 42254381(S)-N-tert-butylcarbonylalanine

Product 1

HCID 123935L-Alanyl-L-GlutamineYield 52%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 1140TolueneSolvent2×HCID 3283Diethyl EtherSolvent2×

Procedure

Dissolve 10 mmol of triphenylphosphine with 10 ml of toluene, drop it into a mixed system composed of 10 mmol of tert-butylcarbonylalanine (Boc-Ala), 10 mmol of hexachloroethane and 20 ml of toluene. After reacting at 5° C. for 2 hours, drop it into a liquid mixture containing 15 mmol of glutamine, 20 ml of water and 60 ml of petrolium ether. While reacting, regulate pH to 12 with sodium hydroxide, the reaction temperature is 10° C., the reaction time after dropping is 1.5 hours. And then acidify it to regulate pH=1.5 with dilute sulfuric acid. The aqueous phase, after concentrated, reacts with hydrogen chloride/1,4-dioxane at room temperature for 5 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 1,4-dioxane-water.

Workup

  1. customis 10° C.
  2. waitthe reaction time after dropping is 1.5 hours
  3. concentrationThe aqueous phase, after concentrated
  4. customreacts with hydrogen chloride/1,4-dioxane at room temperature for 5 hours

Sources & evidence

ORD record
ord-94244808a4d9472a86365f7aa30787d9
Source dataset
uspto-grants-2007_01
Patent number
US07163917B2

Reaction notes

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