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

HRID 927345Notes

Reaction equation

HRID 927345 reaction equation
[CH3:1][C:2]([C:5]([OH:7])=[O:6])([CH3:4])[NH2:3].[OH-].[Na+].Cl[C:11]([O:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[O:12]>O>[CH2:14]([O:13][C:11]([NH:3][C:2]([CH3:4])([CH3:1])[C:5]([OH:7])=[O:6])=[O:12])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

5

Reactant 3

HCID 6119Aminoisobutyric acidHCID 10387Benzyl chloroformateHCID 14798Sodium Hydroxide

Product 1

HCID 294936N-((Benzyloxy)carbonyl)-2-methylalanineYield 36.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of 2-methylalanine (CAN 62-57-7, 30.9 g, 0.3 mol) and sodium hydroxide (20 g, 0.5 mol) in water (500 mL) was added benzyl chloroformate (61.4 g, 0.36 mol) at ice-water bath temperature. The reaction mixture was allowed to warm to room temperature and stirred overnight. The resulting solution was washed with ethyl acetate (2×80 mL), then the aqueous layer was adjusted to pH=2 with conc. hydrochloric acid and the solution was extracted with ethyl acetate (3×150 mL). The combined organic layers were dried over anhydrous sodium sulfate and concentrated under reduced pressure to give the crude target compound (26 g, 36%) which was used directly for the next step without further purification; MS: m/e 238.0 [M+H]+.

Workup

  1. washThe resulting solution was washed with ethyl acetate (2×80 mL)
  2. extractionthe solution was extracted with ethyl acetate (3×150 mL)
  3. dry with materialThe combined organic layers were dried over anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-58aa058080ac4ec8a2a149e2b9940b02
Source dataset
uspto-grants-2016_03
Patent number
US09290451B2

Reaction notes

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