Potassium Carbonate → HCID 69280848, compound

HRID 1396302Notes

Reaction equation

HRID 1396302 reaction equation
C([O:9][CH2:10][C@@H:11]1[C@@H:22]2[C@H:18]([O:19][C:20]([CH3:24])([CH3:23])[O:21]2)[C@@H:17]2[C@@H:13]([S:14][C:15]([N:25]([CH3:27])[CH3:26])=[N:16]2)[O:12]1)(=O)C1C=CC=CC=1.C(=O)([O-])[O-].[K+].[K+]>CO>[CH3:26][N:25]([CH3:27])[C:15]1[S:14][C@@H:13]2[C@@H:17]([C@@H:18]3[C@@H:22]([C@@H:11]([CH2:10][OH:9])[O:12]2)[O:21][C:20]([CH3:23])([CH3:24])[O:19]3)[N:16]=1

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 69280805HCID 69280805, compound

Product 1

HCID 69280848HCID 69280848, compoundYield 90.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 155 (4.0 g, 10 mmol) in methanol (30 mL) was added potassium carbonate (704 mg, 5.1 mmol). The resulting solution was stirred for 2 hours at room temperature, before the reaction was quenched by the addition of water (20 mL), which was then extracted with dichloromethane (3×20 mL). The combined organic layer was washed with brine (2×10 mL), dried over sodium sulfate, filtered and concentrated under vacuum. The crude residue was purified by flash column chromatography with 1%-5% methanol in dichloromethane to afford the title compound as a white solid (2.6 g, 88%). (ES, m/z): [M+H]+ 289.0; 1H NMR (300 MHz, CDCl3) δ 6.34 (d, J=6.0 Hz, 1H), 4.37-4.32 (m, 1H), 4.11-4.05 (m, 1H), 3.94-3.82 (m, 2H), 3.61-3.54 (m, 1H), 3.36-3.23 (m, 1H), 3.08 (s, 6H), 1.46 (s, 6H).

Workup

  1. customwas quenched by the addition of water (20 mL), which
  2. extractionwas then extracted with dichloromethane (3×20 mL)
  3. washThe combined organic layer was washed with brine (2×10 mL)
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under vacuum
  7. customThe crude residue was purified by flash column chromatography with 1%-5% methanol in dichloromethane

Sources & evidence

ORD record
ord-81588d947dbb4ae0bc3325faaece63b1
Source dataset
uspto-grants-2014_12
Patent number
US08901087B2

Reaction notes

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