Potassium Iodide → Glycine, N-(2,2-difluoroethyl)-, ethyl ester
Reaction equation
[F:1][CH:2]([F:5])[CH2:3][NH2:4].Br[CH2:7][C:8]([O:10][CH2:11][CH3:12])=[O:9].[I-].[K+].C(N(C(C)C)CC)(C)C>C(#N)C>[F:1][CH:2]([F:5])[CH2:3][NH:4][CH2:7][C:8]([O:10][CH2:11][CH3:12])=[O:9]Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
2,2-difluoroethylamine (4.0 g) was added to a suspension of ethyl bromoacetate (5.4 mL), potassium iodide (0.82 g), diisopropylethylamine (9.8 mL) in acetonitrile (100 mL) and the mixture was stirred at RT for 25 h. The mixture was concentrated under reduced pressure. The residue was purified by flash column chromatography on silica gel to afford the sub-title compound (7.0 g) as a colorless oil; 1H NMR (300 MHz, CDCl3); 5.82 (1H, tt), 4.18 (2H, q), 3.46 (2H, s), 3.00 (2H, dt), 1.26 (3H, t).
Workup
- concentrationThe mixture was concentrated under reduced pressure
- customThe residue was purified by flash column chromatography on silica gel
Sources & evidence
- ORD record
- ord-b053c74e468b4549b3254fe9cae52beb
- Source dataset
- uspto-grants-2016_06
- Patent number
- US09376398B2
Reaction notes
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