Methanol → HCID 24880320, compound

HRID 529267Notes

Reaction equation

HRID 529267 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]2[C:10]([C:11](=[O:24])[C:12]3[CH:17]=[C:16]([O:18][CH3:19])[C:15]([O:20][CH3:21])=[C:14]([O:22][CH3:23])[CH:13]=3)=[C:9]([CH3:25])[S:8][C:7]=2[C:26]=1[O:27]S(C1C=CC(C)=CC=1)(=O)=O.CO.C(C(O)=O)(F)(F)F>C1COCC1.[OH-].[Na+]>[OH:27][C:26]1[C:7]2[S:8][C:9]([CH3:25])=[C:10]([C:11](=[O:24])[C:12]3[CH:17]=[C:16]([O:18][CH3:19])[C:15]([O:20][CH3:21])=[C:14]([O:22][CH3:23])[CH:13]=3)[C:6]=2[CH:5]=[CH:4][C:3]=1[O:2][CH3:1]

Participants

6

Reactant 3

HCID 887MethanolHCID 6422Trifluoroacetic acidHCID 59138497HCID 59138497, compound

Product 1

HCID 24880320HCID 24880320, compoundYield 279.4%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 14798Sodium HydroxideSolvent

Conditions

Temperature
30 °C

Procedure

A mixture of the product of Example 41 (0.035 g; 0.00645 mmol) in THF (0.5 ml) and 1% NaOH in MeOH (0.52 ml; 0.0129 mmol) was stirred overnight at 30° C. under N2 and acidified with the drop of CF3CO2H. This was evaporated to dryness and diluted to 15 ml with diethyl ether, washed with 0.1 M HCl (2 ml), 5% NaHCO3 (2 ml), brine, dried over anhydrous MgSO4, filtered and filtrate evaporated to dryness under reduced pressure. The residue was purified by flash column chromatography (SiO2, CH2Cl2) to give pure title compound (0.007 g; 28%), as a colourless crystals.

Workup

  1. customThis was evaporated to dryness
  2. additiondiluted to 15 ml with diethyl ether
  3. washwashed with 0.1 M HCl (2 ml), 5% NaHCO3 (2 ml), brine
  4. dry with materialdried over anhydrous MgSO4
  5. filtrationfiltered
  6. customfiltrate evaporated to dryness under reduced pressure
  7. customThe residue was purified by flash column chromatography (SiO2, CH2Cl2)

Sources & evidence

ORD record
ord-52058b4d686242f18b2e7fd9a48822b9
Source dataset
uspto-grants-2016_05
Patent number
US09346842B2

Reaction notes

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