Aminoisobutyric acid → N-((Benzyloxy)carbonyl)-2-methylalanine

HRID 1424211Notes

Reaction equation

HRID 1424211 reaction equation
[CH3:1][C:2]([C:5]([OH:7])=[O:6])([CH3:4])[NH2:3].C([O-])([O-])=O.[Na+].[Na+].[C:14](Cl)([O:16][CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)=[O:15]>O.O1CCOCC1>[CH2:17]([O:16][C:14]([NH:3][C:2]([CH3:4])([C:5]([OH:7])=[O:6])[CH3:1])=[O:15])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

6

Reactant 3

HCID 6119Aminoisobutyric acidHCID 10340Sodium CarbonateHCID 10387Benzyl chloroformate

Product 1

HCID 294936N-((Benzyloxy)carbonyl)-2-methylalanine

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

To a solution of 2-methylalanine (50 g, 0.49 mmol) and Na2CO3 (156 g, 1.47 mol) in water (1 L) was added a solution of CbzCl (91 g, 0.54 mmol) in dioxane (500 mL) at 0° C. over 15 minutes. The resulting solution was stirred at room temperature for 18 hours. The reaction was extracted with Et2O (2×500 mL), and the aqueous layer collected, acidified to pH=1 with cHCl and extracted with EtOAc (2×500 mL). The organic layers were combined, washed with brine, dried over Na2SO4 and concentrated in vacuo to afford a white solid as the title compound that was used directly in the next step (111 g, 97%).

Workup

  1. extractionThe reaction was extracted with Et2O (2×500 mL)
  2. customthe aqueous layer collected
  3. extractionextracted with EtOAc (2×500 mL)
  4. washwashed with brine
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-6e2174996d544325ac54ab4a6acf9b27
Source dataset
uspto-grants-2015_01
Patent number
US08927587B2

Reaction notes

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