Selectfluor → HCID 67066280, compound

HRID 508335Notes

Reaction equation

HRID 508335 reaction equation
[C:1]([C:5]1[C:6]([O:25][CH3:26])=[C:7]([CH:12]=[C:13]([NH:15][C:16]([NH:18][C:19](=[O:24])/[CH:20]=[CH:21]/[O:22][CH3:23])=[O:17])[CH:14]=1)[C:8]([O:10][CH3:11])=[O:9])([CH3:4])([CH3:3])[CH3:2].[B-](F)(F)(F)[F:28].[B-](F)(F)(F)F.C1[N+]2(CCl)CC[N+](F)(CC2)C1>C(#N)C.CO.O>[C:1]([C:5]1[C:6]([O:25][CH3:26])=[C:7]([CH:12]=[C:13]([N:15]2[CH:21]([O:22][CH3:23])[CH:20]([F:28])[C:19](=[O:24])[NH:18][C:16]2=[O:17])[CH:14]=1)[C:8]([O:10][CH3:11])=[O:9])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 2

HCID 2724933SelectfluorHCID 67066357HCID 67066357, compound

Product 1

HCID 67066280HCID 67066280, compoundYield 29%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 6342AcetonitrileSolvent

Conditions

Temperature
90 °C

Procedure

The fluorination procedure was performed as described in Lal, G S, et al. J. Org. Chem., 60:7340-7342 (1995). The product from Example 41A, Part B (0.42 g, 1.26 mmol) and Selectfluor™ (0.672 g, 1.9 mmol) were combined in a mixture of acetonitrile (8 mL) and methanol (1 mL) and heated at 90° C. under N2 for 5 h. The solution was diluted with water, extracted into ethyl acetate, washed with sodium bicarbonate solution, concentrated and purified by column chromatography on silica gel to give the title compound (0.138 g, 29%).

Workup

  1. extractionextracted into ethyl acetate
  2. washwashed with sodium bicarbonate solution
  3. concentrationconcentrated
  4. custompurified by column chromatography on silica gel

Sources & evidence

ORD record
ord-7f0f16cacdd847f28f884105bd53479a
Source dataset
uspto-grants-2015_08
Patent number
US09095590B2

Reaction notes

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