Methanol → HCID 67008022, compound

HRID 1672428Notes

Reaction equation

HRID 1672428 reaction equation
CN(C)[CH:3]=[O:4].FC(F)(F)S(O[C:12]1[CH:13]([CH3:25])[CH2:14][N:15]([C:18]2[C:23]([CH3:24])=[CH:22][CH:21]=[CH:20][N:19]=2)[CH2:16][CH:17]=1)(=O)=O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(N(CC)CC)C.[CH3:54][OH:55]>C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH3:25][CH:13]1[C:12]([C:54]([O:4][CH3:3])=[O:55])=[CH:17][CH2:16][N:15]([C:18]2[C:23]([CH3:24])=[CH:22][CH:21]=[CH:20][N:19]=2)[CH2:14]1

Participants

7

Reactant 5

HCID 887MethanolHCID 6228DimethylformamideHCID 8471TriethylamineHCID 11776TriphenylphosphineHCID 86628448HCID 86628448, compound

Product 1

HCID 67008022HCID 67008022, compound

Reagents, catalysts & solvents 1

HCID 167845palladium(II) acetateCatalyst

Procedure

To a 1:1 mixture of N,N-dimethylformamide: methanol saturated with CO, was added the product from Example 9C (5.29 g, 15.6 mmol), palladium (II) acetate (0.088 g, 0.39 mmol), triphenylphosphine (0.31 g, 1.2 mmol) and triethylamine (4.3 ml, 31 mmol). The reaction was stirred overnight at room temperature under a CO atmosphere. The mixture was then partitioned between water and ether and the organic layer was washed with brine then dried over Na2SO4, filtered, and concentrated under reduced pressure. The residue was purified via silica gel chromatography (gradient elution, 0 to 30% diethyl ether-hexanes) to provide the title compound. MS (DCI/NH3) m/e 247 (M+H)+.

Workup

  1. customThe mixture was then partitioned between water and ether
  2. washthe organic layer was washed with brine
  3. dry with materialthen dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified via silica gel chromatography (gradient elution, 0 to 30% diethyl ether-hexanes)

Sources & evidence

ORD record
ord-21327b50f38f43f9aa05977fda542b5e
Source dataset
uspto-grants-2011_08
Patent number
US07998982B2

Reaction notes

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