Potassium Iodide → Glycine, N-(2,2-difluoroethyl)-, ethyl ester

HRID 2207069Notes

Reaction equation

HRID 2207069 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

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

  1. concentrationThe mixture was concentrated under reduced pressure
  2. 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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