DL-valine → Tert-butyl 2-amino-3-methylbutanoate

HRID 572552Notes

Reaction equation

HRID 572552 reaction equation
[NH2:1][CH:2]([C:6]([OH:8])=[O:7])[CH:3]([CH3:5])[CH3:4]>C(OC(C)(C)C)(=O)C.O>[NH2:1][CH:2]([CH:3]([CH3:5])[CH3:4])[C:6]([O:8][C:3]([CH3:5])([CH3:4])[CH3:2])=[O:7]

Participants

4

Reactant 1

HCID 1182DL-valine

Product 1

HCID 4532027Tert-butyl 2-amino-3-methylbutanoate

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 10908tert-Butyl acetateSolvent

Procedure

To a stirred solution of DL-valine (25 g, 0.213 mol) in tert-butyl acetate (250 mL) at 00° C., was added HClO4 (64.2 g, 0.320 mol) portionwise. The reaction mixture was stirred for 36 h at RT. It was diluted with water and extracted in ethyl acetate (500 mL). The organic layer was washed with a 10% sodium bicarbonate solution (2×150 mL), dried over Na2SO4 and concentrated, affording of the title compound as brown liquid. 1H NMR (DMSO-d6, 400 MHz) δ 7.31 (brs, 2H), 3.62 (d, J=4.4 Hz, 1H), 1.98 (d, J=1.7 Hz, 1H), 1.44 (s, 9H), 0.95 (m, 6H).

Workup

  1. extractionextracted in ethyl acetate (500 mL)
  2. washThe organic layer was washed with a 10% sodium bicarbonate solution (2×150 mL)
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-c394bcdcf3414ee8b470c0b7e3dfa761
Source dataset
uspto-grants-2015_05
Patent number
US09029405B2

Reaction notes

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