Water → HCID 53822480, compound

HRID 1004621Notes

Reaction equation

HRID 1004621 reaction equation
F[C:2](F)(F)[C:3](O)=O.[Si:8]([O:15][C@H:16]([C@H:19]1[C@@H:22]([C:23]#[C:24][S:25]C2C=CC=CC=2)[NH:21][C:20]1=[O:32])[CH2:17][CH3:18])([C:11]([CH3:14])([CH3:13])[CH3:12])([CH3:10])[CH3:9].C(=O)([O-])O.[Na+].O>C(Cl)Cl.C(OCC)(=O)C>[Si:8]([O:15][C@H:16]([C@H:19]1[C@@H:22]([CH2:23][C:24]([C:3]2[CH:2]=[CH:18][CH:17]=[CH:16][CH:19]=2)=[S:25])[NH:21][C:20]1=[O:32])[CH2:17][CH3:18])([C:11]([CH3:12])([CH3:13])[CH3:14])([CH3:9])[CH3:10]

Participants

7

Reactant 4

HCID 962WaterHCID 6422Trifluoroacetic acidHCID 516892Sodium BicarbonateHCID 53804451HCID 53804451, compound

Product 1

HCID 53822480HCID 53822480, compoundYield 152.5%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent2×

Procedure

Trifluoroacetic acid (0.58 ml, 7.51 mmol) was added to a solution of the compound (564 mg, 1.50 mmol) prepared in Example 6 in methylene chloride (10 ml) at 0° C. in an argon atmosphere. The mixture was stirred for two hours at this temperature and one hour at room temperature. After the addition of sodium hydrogencarbonate (189 mg, 2.25 mmol), water (7 ml), and ethyl acetate (28 ml), the mixture was stirred at room temperature for 40 minutes and diluted with ethyl acetate. The organic layer was washed with a saturated aqueous solution of sodium hydrogencarbonate and saturated brine in this order and dried over anhydrous sodium sulfate. The solvent was removed by evaporation under reduced pressure and the residue was purified by silica gel chromatography (hexane/ethyl acetate=3/1) to obtain 432 mg (yield 73%) of the title compound as a colorless oily substance.

Workup

  1. stirringthe mixture was stirred at room temperature for 40 minutes
  2. washThe organic layer was washed with a saturated aqueous solution of sodium hydrogencarbonate and saturated brine in this order
  3. dry with materialdried over anhydrous sodium sulfate
  4. customThe solvent was removed by evaporation under reduced pressure
  5. customthe residue was purified by silica gel chromatography (hexane/ethyl acetate=3/1)

Sources & evidence

ORD record
ord-89368070293b404c8c9187ea8263da2e
Source dataset
uspto-grants-2000_04
Patent number
US06051569

Reaction notes

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