Gamma-Aminobutyric Acid → 4-(((Tert-butoxy)carbonyl)amino)butanoic acid

HRID 388855Notes

Reaction equation

HRID 388855 reaction equation
[NH2:1][CH2:2][CH2:3][CH2:4][C:5]([OH:7])=[O:6].[OH-].[Na+].[O:10](C(OC(C)(C)C)=O)[C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=O>CC(O)(C)C.O>[C:14]([O:13][C:11]([NH:1][CH2:2][CH2:3][CH2:4][C:5]([OH:7])=[O:6])=[O:10])([CH3:17])([CH3:16])[CH3:15]

Participants

6

Reactant 3

HCID 119Gamma-Aminobutyric AcidHCID 14798Sodium HydroxideHCID 90495Di-tert-butyl dicarbonate

Product 1

HCID 2948944-(((Tert-butoxy)carbonyl)amino)butanoic acidYield 85%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6386tert-ButanolSolvent

Procedure

To a solution of γ-aminobutyric acid (1 equivalent) in t-BuOH (4 ml/gram) and H2O (3 ml/gram) was added NaOH (1 equivalent), BOC2O (1 equivalent), and the mixture was stirred at room temperature for 24 hours. The solvent was thereafter evaporated and the residue was partitioned between hexane and water. The aqueous layer was acidified with KHSO41N to reach pH=2, and was thereafter extracted with CH2Cl2. The organic layer was dried over MgSO4 and the solvent was evaporated to give the desired product as a white solid (85% yield).

Workup

  1. customThe solvent was thereafter evaporated
  2. customthe residue was partitioned between hexane and water
  3. extractionwas thereafter extracted with CH2Cl2
  4. dry with materialThe organic layer was dried over MgSO4
  5. customthe solvent was evaporated

Sources & evidence

ORD record
ord-d22a41bb90844dd9b9906dedf0312d33
Source dataset
uspto-grants-2013_02
Patent number
US08377990B2

Reaction notes

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