Acetic Anhydride → HCID 57446943, compound

HRID 1620930Notes

Reaction equation

HRID 1620930 reaction equation
Cl.[F:2][C:3]([F:13])([F:12])[CH:4]([CH3:11])[CH2:5][C@@H:6]([C:8]([OH:10])=[O:9])[NH2:7].[OH-].[Na+].[C:16](OC(=O)C)(=[O:18])[CH3:17]>O>[C:16]([NH:7][C@H:6]([C:8]([OH:10])=[O:9])[CH2:5][CH:4]([C:3]([F:12])([F:13])[F:2])[CH3:11])(=[O:18])[CH3:17]

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 14798Sodium HydroxideHCID 713598465,5,5-Trifluoro-L-leucine--hydrogen chloride (1/1)

Product 1

HCID 57446943HCID 57446943, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a cold (0° C.) solution of the 5,5,5-trifluoroleucine HCl salt (from Step 1 above) in H2O (30 mL) was added 1M aqueous NaOH (60 mL, 60 mmol) followed by acetic anhydride (3.5 mL, 36.7 mmol). The mixture was stirred at room temperature for 30 min to 1 h. After acidification with 6M aqueous HCl (6 mL), the mixture was extracted with EtOAc (6×). The combined EtOAc extracts were washed with brine, dried (MgSO4) and concentrated. The residue was swished with hexanes:Et2O (1:1) to afford N-acetyl-5,5,5-trifluoroleucine as a white solid.

Workup

  1. extractionAfter acidification with 6M aqueous HCl (6 mL), the mixture was extracted with EtOAc (6×)
  2. washThe combined EtOAc extracts were washed with brine
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-1097263f507643e28a936edefcb5f73f
Source dataset
uspto-grants-2014_07
Patent number
US08772336B2

Reaction notes

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