Methanol → HCID 131728126, compound

HRID 2237762Notes

Reaction equation

HRID 2237762 reaction equation
CS[C:3]1[CH:4]=[CH:5][C:6]2[N:10]=[C:9]3[CH2:11][CH:12]([C:23]4[CH:28]=[C:27]([F:29])[C:26]([F:30])=[CH:25][C:24]=4[F:31])[CH:13]([NH:15][C:16](=[O:22])[O:17][C:18]([CH3:21])([CH3:20])[CH3:19])[CH2:14][N:8]3[C:7]=2[CH:32]=1.O[O:34][S:35]([O-:37])=O.[K+].[CH3:39]O>C(OCC)(=O)C>[C:18]([O:17][C:16](=[O:22])[NH:15][C@H:13]1[CH2:14][N:8]2[C:9](=[N:10][C:6]3[CH:5]=[CH:4][C:3]([S:35]([CH3:39])(=[O:37])=[O:34])=[CH:32][C:7]=32)[CH2:11][C@@H:12]1[C:23]1[CH:28]=[C:27]([F:29])[C:26]([F:30])=[CH:25][C:24]=1[F:31])([CH3:19])([CH3:20])[CH3:21]

Participants

5

Reactant 3

HCID 887MethanolHCID 23707502Potassium hydroxy sulfiteHCID 90715826HCID 90715826, compound

Product 1

HCID 131728126HCID 131728126, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a solution containing 41 mg (0.088 mmol) of the product from Step B in 6.0 mL of methanol was added 160 mg (0.26 mmol) of oxone as a 2 mL aqueous solution. The reaction mixture was stirred at ambient temperature for 16 h, then diluted with 50 mL of ethyl acetate and washed sequentially with 0.5N aqueous sodium bicarbonate solution and saturated aqueous brine (50 mL each), dried over sodium sulfate, filtered and the solvent evaporated in vacuo to yield a crude solid. Purification by reverse phase HPLC (YMC Pro-C18 column, gradient elution, 5% to 80% acetonitrile/water with 0.1% TFA) afforded the pure title compound as a white foam. LC/MS 496.1 (M+1).

Workup

  1. washwashed sequentially with 0.5N aqueous sodium bicarbonate solution and saturated aqueous brine (50 mL each)
  2. dry with materialdried over sodium sulfate
  3. filtrationfiltered
  4. customthe solvent evaporated in vacuo
  5. customto yield a crude solid
  6. customPurification
  7. washby reverse phase HPLC (YMC Pro-C18 column, gradient elution, 5% to 80% acetonitrile/water with 0.1% TFA)

Sources & evidence

ORD record
ord-07fcd600fd52489eab004a509833fcf8
Source dataset
uspto-grants-2010_05
Patent number
US07718667B2

Reaction notes

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