Methanesulfonic Acid → HCID 59550553, compound

HRID 1169585Notes

Reaction equation

HRID 1169585 reaction equation
[CH2:1]([O:3][C:4]([C:6]1([CH2:28][CH2:29][CH2:30][C:31]([O:33][CH2:34][CH3:35])=[O:32])[CH2:12][CH2:11][N:10]([S:13]([C:16]2[CH:21]=[CH:20][C:19]([CH3:22])=[CH:18][CH:17]=2)(=[O:15])=[O:14])[C:9]2[CH:23]=[CH:24][CH:25]=[CH:26][C:8]=2[C:7]1=O)=[O:5])[CH3:2].FC(F)(F)C(O)=O.B(F)(F)F.CCOCC.CS(O)(=O)=O.C([SiH](CC)CC)C>ClCCCl>[CH2:1]([O:3][C:4]([C:6]1([CH2:28][CH2:29][CH2:30][C:31]([O:33][CH2:34][CH3:35])=[O:32])[CH2:12][CH2:11][N:10]([S:13]([C:16]2[CH:17]=[CH:18][C:19]([CH3:22])=[CH:20][CH:21]=2)(=[O:15])=[O:14])[C:9]2[CH:23]=[CH:24][CH:25]=[CH:26][C:8]=2[CH2:7]1)=[O:5])[CH3:2]

Participants

7

Reactant 5

HCID 6395Methanesulfonic AcidHCID 6422Trifluoroacetic acidHCID 8000Boron trifluoride etherateHCID 12052TriethylsilaneHCID 24964978HCID 24964978, compound

Product 1

HCID 59550553HCID 59550553, compoundYield 53%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Conditions

Temperature
5 °C

Procedure

Compound 28 (4.76 g, 9.48 mmol) was dissolved in 45 mL of dry 1,2-dichloroethane, cooled to 5° C., and treated with trifluoroacetic acid (1.3 mL), BF3.Et2O (1.4 mL), anhydrous methanesulfonic acid (3.2 mL) and triethylsilane (5.7 mL). The reaction was allowed to slowly warm to room temperature over 18 hours. The reaction was cooled to 5° C. and cautiously quenched with saturated aqueous NaHCO3 (100 mL). The reaction mixture was extracted with ethyl acetate (100 mL) and the ethyl acetate extract was extracted with saturated aqueous NaHCO3, water, brine (2×), dried over Na2SO4, and concentrated in vacuo to give an oil. This oil was purified by column chromatography on silica gel eluting with hexane/ethyl acetate (17:3) to give 2.43 g (53%) of compound 29 as a colorless oil.

Workup

  1. temperatureto slowly warm to room temperature over 18 hours
  2. temperatureThe reaction was cooled to 5° C.
  3. customcautiously quenched with saturated aqueous NaHCO3 (100 mL)
  4. extractionThe reaction mixture was extracted with ethyl acetate (100 mL)
  5. extractionthe ethyl acetate extract
  6. extractionwas extracted with saturated aqueous NaHCO3, water, brine (2×)
  7. dry with materialdried over Na2SO4
  8. concentrationconcentrated in vacuo
  9. customto give an oil
  10. customThis oil was purified by column chromatography on silica gel eluting with hexane/ethyl acetate (17:3)

Sources & evidence

ORD record
ord-10274885fac141b08444a50eb1390f43
Source dataset
uspto-grants-2010_11
Patent number
US07825111B2

Reaction notes

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