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Gamma-Aminobutyric Acid → Glutamic acid, 5-(1,1-dimethylethyl) ester

HRID 732865
Notes
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Reaction equation

HRID 732865 reaction equation
[NH2:1][CH2:2][CH2:3][CH2:4][C:5]([OH:7])=[O:6].[OH-].[Na+].C([O:14][C:15](OC(OC(C)(C)C)=O)=[O:16])(C)(C)C.O.[C:26](O)([CH3:29])([CH3:28])[CH3:27]>>[C:5]([CH2:4][CH2:3][CH:2]([NH2:1])[C:15]([OH:16])=[O:14])([O:7][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:6]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 5

HCID 119Gamma-Aminobutyric AcidHCID 962WaterHCID 6386tert-Butanol2×HCID 14798Sodium HydroxideHCID 90495Di-tert-butyl dicarbonate

Product 1

HCID 3431852Glutamic acid, 5-(1,1-dimethylethyl) ester

Procedure

4-Aminobutanoic acid (1 g, 9.7 mmol) was dissolved in tert-butyl alcohol (15 ml), 5N NaOH (1.93 ml, 9.7 mmol) was added thereto, and the mixture was stirred at room temperature for 10 minutes. Di-tert-butyl-dicarbonate (2.33 g, 10.7 mmol) dissolved in tert-butylalcohol (17 ml) was added thereto and stirred for 24 hours at room temperature. Water (12 ml) was added thereto and the resultant was concentrated under a reduced pressure and cooled to 0° C. Then, 2N H2SO4 was added thereto dropwise until pH of the mixture became 2. The resultant was extracted with ethyl acetate and the extract was washed with water. The organic layer was dried over MgSO4 and concentrated to obtain the title compound (2.1 g) as a white solid.

Workup

  1. additionwas added
  2. stirringstirred for 24 hours at room temperature
  3. concentrationthe resultant was concentrated under a reduced pressure
  4. temperaturecooled to 0° C
  5. additionThen, 2N H2SO4 was added
  6. extractionThe resultant was extracted with ethyl acetate
  7. washthe extract was washed with water
  8. dry with materialThe organic layer was dried over MgSO4
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-0eaaf035a053449f9a730905a7037da5
Source dataset
uspto-grants-2009_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07589072B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes