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

HRID 2207069
Notes
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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]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 7748Ethyl bromoacetateHCID 81531DiisopropylethylamineHCID 1362742,2-Difluoroethanamine

Product 1

HCID 60921893Glycine, N-(2,2-difluoroethyl)-, ethyl ester

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

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
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09376398B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes