Ethyl Acetate → (R)-2-(3-bromo-4-cyanophenylamino)propanamide

HRID 84807

Reaction equation

HRID 84807 reaction equation
[Br:1][C:2]1[CH:9]=[C:8](F)[CH:7]=[CH:6][C:3]=1[C:4]#[N:5].Cl.[NH2:12][C@@H:13]([C:15]([NH2:17])=[O:16])[CH3:14].CC(N(C)C)=O.CCOC(C)=O>CS(C)=O.O>[Br:1][C:2]1[CH:9]=[C:8]([NH:12][C@H:13]([CH3:14])[C:15]([NH2:17])=[O:16])[CH:7]=[CH:6][C:3]=1[C:4]#[N:5]

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 31374DimethylacetamideHCID 1189392-Bromo-4-fluorobenzonitrileHCID 2775814(2R)-2-Aminopropanamide hydrochloride

Product 1

HCID 67509792(R)-2-(3-bromo-4-cyanophenylamino)propanamideYield 69%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Procedure

A solution of 2-bromo-4-fluorobenzonitrile (200 mg, 1.00 mmol), D-alanine amide hydrochloride (148 mg, 1.19 mmol) and DMA (0.620 mL, 3.56 mmol) in DMSO (3 mL) was stirred at 100 C for 18 h. EtOAc and water were added. The organic phase was separated, dried over Na2SO4, concentrated in vacuo. The residue was purified by a silica gel column, eluted first with 30% EtOAc in hexane, then with 100% EtOAc to give (R)-2-(3-bromo-4-cyanophenylamino)propanamide (185 mg).

Workup

  1. customThe organic phase was separated
  2. dry with materialdried over Na2SO4
  3. concentrationconcentrated in vacuo
  4. customThe residue was purified by a silica gel column
  5. washeluted first with 30% EtOAc in hexane

Sources & evidence

ORD record
ord-b944b628013f4510976ce132dfb416ca
Source dataset
uspto-grants-2014_09
Patent number
US08846928B2

Linked notes

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