Ethylamine → L-Theanine

HRID 1925781Notes

Reaction equation

HRID 1925781 reaction equation
CO[C:3]([CH2:5][CH2:6][C@H:7]([NH2:11])[C:8]([OH:10])=[O:9])=[O:4].C1(C(O)CC(O)C)C=CC=CC=1.[CH2:24]([N:26](CC)CC)[CH3:25].C(N)C>CO>[NH2:11][C@H:7]([C:8]([OH:10])=[O:9])[CH2:6][CH2:5][C:3]([NH:26][CH2:24][CH3:25])=[O:4]

Participants

6

Reactant 4

HCID 6341EthylamineHCID 8471TriethylamineHCID 686625-Methyl hydrogen L-glutamateHCID 5232872HCID 5232872, compound

Product 1

HCID 439378L-TheanineYield 87%

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, 5.6 g (34 mmol) of 1-phenyl-1,3-butanediol and 3.1 g (31 mmol) of triethylamine were added. The mixture was heated at 60° C. for 2 hours. Subsequently, 20 g (310 mmol) of 70% ethylamine was added to the mixture and the same procedure as in Example 1 was performed to obtain 4.7 g of theanine (yield: 87%). The obtained theanine had the same purity as high as in Example 1.

Sources & evidence

ORD record
ord-d879e0f5ebf14851a5e7d043e2afb4b7
Source dataset
uspto-grants-2012_05
Patent number
US08178722B2

Reaction notes

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