Acetic Acid → L-Theanine

HRID 1925782Notes

Reaction equation

HRID 1925782 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.[CH2:23]([NH2:25])[CH3:24]>C1(C)C=CC=CC=1>[NH2:11][C@H:7]([C:8]([OH:10])=[O:9])[CH2:6][CH2:5][C:3]([NH:25][CH2:23][CH3:24])=[O:4]

Participants

6

Reactant 4

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

Product 1

HCID 439378L-TheanineYield 5.5%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

First, 5.0 g (31 mmol) of L-glutamic acid-γ-methyl ester was suspended in 45 g of toluene. To this, 15 g (233 mmol) of acetylacetone and 5.6 g (93 mmol) of acetic acid were added. The mixture was heated for 2 hours while removing water generated by use of an ester tube at 100° C. to 110° C. The solvent was removed to obtain 7.9 g of a yellow oily substance. To the oily substance, 13.5 g (210 mmol) of 70% ethylamine was added and allowed to react for 23 hours. The same procedure as in Example 1 was performed to obtain 0.2 g of theanine (yield: 5.5%).

Workup

  1. temperatureThe mixture was heated for 2 hours
  2. customwhile removing water
  3. customgenerated by use of an ester tube at 100° C. to 110° C
  4. customThe solvent was removed
  5. customto obtain 7.9 g of a yellow oily substance
  6. customto react for 23 hours

Sources & evidence

ORD record
ord-11047674caf64cc0866042d4b4904e0e
Source dataset
uspto-grants-2012_05
Patent number
US08178722B2

Reaction notes

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