Dimethylformamide → HCID 25417937, compound

HRID 2222624Notes

Reaction equation

HRID 2222624 reaction equation
[C:1]([NH:8][C@@H:9]([CH2:17][OH:18])[CH2:10][C@@H:11]([C:13]([F:16])([F:15])[F:14])[CH3:12])([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].C1C=C[NH+]=CC=1.C1C=C[NH+]=CC=1.[O-:31][Cr](O[Cr]([O-])(=O)=O)(=O)=O.CN(C=O)C>C(OCC)(=O)C.O>[C:1]([NH:8][C@@H:9]([C:17]([OH:31])=[O:18])[CH2:10][C@@H:11]([C:13]([F:16])([F:15])[F:14])[CH3:12])([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2]

Participants

6

Reactant 3

HCID 6228DimethylformamideHCID 2724130Cornforth reagentHCID 86593507HCID 86593507, compound

Product 1

HCID 25417937HCID 25417937, compoundYield 60%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of (2S,4R)-, (2R,4S)-N-Boc-5,5,5-trifluoroleucinol (330 mg, 1.23 mmol), PDC (4.62 g, 12.3 mmol), and dry DMF (2.5 mL) was stirred at room temperature under argon for 4 h, then diluted with 50 mL of ethyl acetate and 50 mL of water. The organic layer was washed with 30 mL of 1N HCl and 2×30 mL of water, dried over MgSO4, and concentrated to give 198 mg of (2S,4R)-, (2R,4S)-N-Boc-5,5,5-trifluoroleucine as a pale-brownish oil (60%).

Workup

  1. washThe organic layer was washed with 30 mL of 1N HCl and 2×30 mL of water
  2. dry with materialdried over MgSO4
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-3ad57e4c18194a2286e76c8be9451486
Source dataset
uspto-grants-2008_05
Patent number
US07371867B2

Reaction notes

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