Aminoisobutyric acid → N-(5-Fluoro-2-nitrophenyl)-2-methylalanine

HRID 1899957Notes

Reaction equation

HRID 1899957 reaction equation
F[C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[N+:9]([O-:11])=[O:10].[NH2:12][C:13]([CH3:18])([CH3:17])[C:14]([OH:16])=[O:15].C(=O)([O-])[O-].[K+].[K+].C(#N)C>O>[F:8][C:6]1[CH:5]=[CH:4][C:3]([N+:9]([O-:11])=[O:10])=[C:2]([NH:12][C:13]([CH3:18])([C:14]([OH:16])=[O:15])[CH3:17])[CH:7]=1

Participants

6

Reactant 4

HCID 6119Aminoisobutyric acidHCID 6342AcetonitrileHCID 11430Potassium CarbonateHCID 679672,4-Difluoronitrobenzene

Product 1

HCID 22912907N-(5-Fluoro-2-nitrophenyl)-2-methylalanine

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 32.62 g of 2,4-difluoronitrobenzene, 24.2 g of 2-aminoisobutyric acid, 15.2 g of potassium carbonate, 100 ml of acetonitrile, and 100 ml of water is heated at 80° for 2 days (until TLC shows little or no starting material). The reaction is then cooled and acetonitrile is removed under reduced pressure. The pH is adjusted to 5 with 4 N hydrochloric acid and the mixture is extracted with chloroform (3×300 ml). The organic layers are dried over sodium sulfate and concentrated. The material is used in the next step without further purification.

Workup

  1. temperatureis heated at 80° for 2 days (until TLC
  2. temperatureThe reaction is then cooled
  3. customacetonitrile is removed under reduced pressure
  4. extractionthe mixture is extracted with chloroform (3×300 ml)
  5. dry with materialThe organic layers are dried over sodium sulfate
  6. concentrationconcentrated
  7. customThe material is used in the next step without further purification

Sources & evidence

ORD record
ord-3bbaa89271f54b50a937e32552777d25
Source dataset
uspto-grants-1996_11
Patent number
US05574038

Reaction notes

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