Methanol → Methyl 2-amino-2-methylbutanoate
Reaction equation
Cl.[NH2:2][C:3]([CH3:9])([CH2:7][CH3:8])[C:4]([OH:6])=[O:5].[CH3:10]O>O1CCOCC1>[NH2:2][C:3]([CH3:9])([CH2:7][CH3:8])[C:4]([O:6][CH3:10])=[O:5]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 50 °C
Procedure
2-amino-2-methylbutanoic acid HCl salt (20 g, 130.2 mmol) was suspended in 150 mL methanol. A solution of HCL (4M in dioxane was added and the mixture heated to 50° C. overnight. The mixture was cooled to room temperature and evaporated to dryness under vacuum. The resulting isovaline methyl ester (20 g) was used without further purification. 1H NMR (300 MHz, DMSO) δ 3.78-3.64 (m, 1H), 3.61 (s, 3H), 3.54-3.41 (m, 1H), 2.50 (d, J=1.6 Hz, 1H), 1.76 (s, 2H), 1.66-1.35 (m, 2H), 1.17 (s, 3H), 0.77 (t, J=7.5 Hz, 3H).
Workup
- temperatureThe mixture was cooled to room temperature
- customevaporated to dryness under vacuum
- customThe resulting isovaline methyl ester (20 g) was used without further purification
Sources & evidence
- ORD record
- ord-047cc89b3d7d47d5921488373f27c8b1
- Source dataset
- uspto-grants-2015_02
- Patent number
- US08946425B2
Reaction notes
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