L-Valine → 2-((Methoxycarbonyl)amino)-3-methylbutanoic acid
Reaction equation
[NH2:1][C@H:2]([C:6]([OH:8])=[O:7])[CH:3]([CH3:5])[CH3:4].C(=O)([O-])[O-].[Na+].[Na+].Cl[C:16]([O:18][CH3:19])=[O:17]>[OH-].[Na+]>[CH3:19][O:18][C:16]([NH:1][CH:2]([CH:3]([CH3:5])[CH3:4])[C:6]([OH:8])=[O:7])=[O:17]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
To a solution of L-valine, d8 (Cambridge Isotope Laboratories, 0.4949 g) in 1N sodium hydroxide (3.95 mL) was added sodium carbonate (0.419 g). The solution was cooled to 0° C. and methyl chloroformate (0.289 mL) was added dropwise over 30 minutes and reaction mixture was stirred for 3 h at 0° C. Reaction mixture was washed with ethyl ether (3×15 mL) and aqueous layer was acidified to pH=1 with concentrated HCl. Aqueous layer was extracted dichloromethane (3×15 mL) and organic layers were dried (MgSO4) and concentrated to give 2-Methoxycarbonylamino-3-methyl-butyric acid, d8 as a white solid (0.5681 g).
Workup
- customreaction mixture
- customReaction mixture
- washwas washed with ethyl ether (3×15 mL) and aqueous layer
- extractionAqueous layer was extracted dichloromethane (3×15 mL) and organic layers
- dry with materialwere dried (MgSO4)
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-9bff8a8c8b9f495b80581e7d6dd20628
- Source dataset
- uspto-grants-2012_09
- Patent number
- US08273341B2
Reaction notes
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