Formic Acid → L-Theanine

HRID 1925774

Reaction equation

HRID 1925774 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.[CH2:19]([N:21](CC)CC)[CH3:20].C(N)C.C(O)=O>CO.CC(O)C>[NH2:11][C@H:7]([C:8]([OH:10])=[O:9])[CH2:6][CH2:5][C:3]([NH:21][CH2:19][CH3:20])=[O:4]

Participants

8

Reactant 5

HCID 284Formic AcidHCID 6341EthylamineHCID 8471TriethylamineHCID 31261AcetylacetoneHCID 686625-Methyl hydrogen L-glutamate

Product 1

HCID 439378L-TheanineYield 82%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 3776IsopropanolSolvent

Conditions

Temperature
60 °C

Procedure

First, 20.0 g (0.124 mol) of L-glutamic acid-γ-methyl ester was suspended in 20 g of methanol. To this, 13.7 g (0.137 mol) of acetylacetone and 12.5 g (0.124 mol) of triethylamine were added. The mixture was stirred at 60° C. for one hour. Subsequently, 80 g (1.24 mol) of 70% ethylamine was added to the mixture. After the mixture was allowed to react for 6 hours, excessive ethylamine was distilled away under reduced pressure. To this, 11.4 g (0.246 mol) of formic acid and 120 mL of 2-propanol (IPA) were added. The crystal precipitated was filtrated by suction and washed with 20 mL of IPA to obtain wet matter. The wet matter was dried under reduced pressure to obtain 17.7 g of theanine as a white crystal substance (yield: 82%).

Workup

  1. customto react for 6 hours
  2. distillationexcessive ethylamine was distilled away under reduced pressure
  3. customThe crystal precipitated
  4. filtrationwas filtrated by suction
  5. washwashed with 20 mL of IPA
  6. customto obtain wet matter
  7. customThe wet matter was dried under reduced pressure

Sources & evidence

ORD record
ord-a804b629c46443cbad14b550f62e952b
Source dataset
uspto-grants-2012_05
Patent number
US08178722B2

Linked notes

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