Acetic Acid → L-Theanine

HRID 1925783Notes

Reaction equation

HRID 1925783 reaction equation
CO[C:3]([CH2:5][CH2:6][C@H:7]([NH2:11])[C:8]([OH:10])=[O:9])=[O:4].C(CC(=O)C)(=O)C.C(O)(=O)C.S([O-])([O-])(=O)=O.[Na+].[Na+].[CH2:30]([NH2:32])[CH3:31]>CO>[NH2:11][C@H:7]([C:8]([OH:10])=[O:9])[CH2:6][CH2:5][C:3]([NH:32][CH2:30][CH3:31])=[O:4]

Participants

7

Reactant 5

HCID 176Acetic AcidHCID 6341EthylamineHCID 24436Sodium SulfateHCID 31261AcetylacetoneHCID 686625-Methyl hydrogen L-glutamate

Product 1

HCID 439378L-TheanineYield 29.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
60 °C

Procedure

First, 5.0 g (31 mmol) of L-glutamic acid-γ-methyl ester was suspended in 15 mL of methanol. To this, 3.4 g (34 mmol) of acetylacetone, 1.9 g (31 mmol) of acetic acid, and 5.0 g of anhydrous sodium sulfate were added. The mixture was heated at 60° C. for 2 hours. Subsequently, sodium sulfate was filtrated off. To the filtrate, 20 g (310 mmol) of 70% ethylamine was added and the same procedure as in Example 1 was performed to obtain 1.6 g of theanine (yield: 29.6%).

Workup

  1. filtrationSubsequently, sodium sulfate was filtrated off

Sources & evidence

ORD record
ord-e51dab4b45b841bcaa22c2b1db0a5a6e
Source dataset
uspto-grants-2012_05
Patent number
US08178722B2

Reaction notes

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