Hydrochloric Acid → L-Alanyl-L-Glutamine

HRID 1373729Notes

Reaction equation

HRID 1373729 reaction equation
C([NH:11][C@H:12]([C:14](O)=[O:15])[CH3:13])(OCC1C=CC=CC=1)=O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.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-].[Na+].Cl>O.C1(C)C=CC=CC=1>[NH2:11][C@H:12]([C:14]([NH:44][C@H:45]([C:51]([OH:53])=[O:52])[CH2:46][CH2:47][C:48](=[O:50])[NH2:49])=[O:15])[CH3:13]

Participants

9

Reactant 6

HCID 313Hydrochloric AcidHCID 5961L-GlutamineHCID 6214HexachloroethaneHCID 11776TriphenylphosphineHCID 14798Sodium HydroxideHCID 736104N-carbobenzyloxyalanine

Product 1

HCID 123935L-Alanyl-L-GlutamineYield 48%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

In a round bottom flask, add in 10 mmol each of carbobenzoxy-alanine (Z-Ala), triphenylphosphine and hexachloroethane respectively, and then 30 ml of toluene. After reacting at 0° C. for 3 h., drop it into a liquid mixture containing 25 mmol of glutamine and 20 ml of water. While reacting, regulate pH to 12 with sodium hydroxide, the reaction temperature is 15° C., the reaction time after dropping is 1.5 hours. And then acidify it to pH=2.5 with dilute hydrochloric acid. The aqueous phase, after concentrated, reacts with hydrogen gas in methanol at room temperature for 15 hours. The product L-Ala-L-Gln with a yield of 48% is obtained.

Workup

  1. customis 15° C.
  2. waitthe reaction time after dropping is 1.5 hours
  3. concentrationThe aqueous phase, after concentrated
  4. customreacts with hydrogen gas in methanol at room temperature for 15 hours

Sources & evidence

ORD record
ord-6643d91c744341a587477ff19123b0ca
Source dataset
uspto-grants-2007_01
Patent number
US07163917B2

Reaction notes

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