L-Leucine → HCID 69151219, compound

HRID 1744046Notes

Reaction equation

HRID 1744046 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([Br:8])=[CH:4][CH:3]=1.[NH2:9][C@H:10]([C:15]([OH:17])=[O:16])[CH2:11][CH:12]([CH3:14])[CH3:13].C(=O)([O-])[O-].[K+].[K+]>[Cu](I)I.CC(N(C)C)=O>[Br:8][C:5]1[CH:6]=[CH:7][C:2]([NH:9][C@@H:10]([CH2:11][CH:12]([CH3:14])[CH3:13])[C:15]([OH:17])=[O:16])=[CH:3][CH:4]=1

Participants

6

Reactant 3

HCID 6106L-LeucineHCID 78041,4-DibromobenzeneHCID 11430Potassium Carbonate

Product 1

HCID 69151219HCID 69151219, compound

Reagents, catalysts & solvents 2

HCID 83717Copper iodideCatalystHCID 31374DimethylacetamideSolvent

Conditions

Temperature
95 °C

Procedure

To 1,4-dibromobenzene (16.1 g, 68.25 mmol), L-leucine (2.984 g, 22.75 mmol), potassium carbonate (4.71 g, 34.13 mmol), and copper iodide (650 mg, 3.41 mmol) was added dry DMA (N,N-dimethylacetamide, 100 mL). The reaction flask was thoroughly degassed with dry nitrogen and heated at 95° C. for 3 days. Water and hexane were added and the organic phase was separated and discarded (to remove excess 1,4-dibromobenzene). The pH of the aqueous phase was adjusted to 3 and the product was extracted with EtOAc (3×), dried on Na2SO4, concentrated in vacuo, and purified by flash chromatography over silica gel (EtOAc/Hex/AcOH, 3/7/1% then 4/6/1%) to afford (2S)-2-(4-bromoanilino)-4-methylpentanoic acid.

Workup

  1. customThe reaction flask was thoroughly degassed with dry nitrogen
  2. additionWater and hexane were added
  3. customthe organic phase was separated
  4. custom(to remove excess 1,4-dibromobenzene)
  5. extractionthe product was extracted with EtOAc (3×)
  6. customdried on Na2SO4
  7. concentrationconcentrated in vacuo
  8. custompurified by flash chromatography over silica gel (EtOAc/Hex/AcOH, 3/7/1%

Sources & evidence

ORD record
ord-88cf1096d652476eaee7d05850b425b4
Source dataset
uspto-grants-2006_03
Patent number
US07012075B2

Reaction notes

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