Methyl iodide → HCID 67200495, compound

HRID 551705Notes

Reaction equation

HRID 551705 reaction equation
[H-].[Na+].O1CCC[CH2:4]1.[C:8]([O:12][C:13]([NH:15][CH2:16][C@@:17]1([CH2:26][C:27]([OH:29])=[O:28])[CH2:23][C@H:22]2[C@@H:18]1[CH:19]=[C:20]([CH2:24][CH3:25])[CH2:21]2)=[O:14])([CH3:11])([CH3:10])[CH3:9].CI>O>[C:8]([O:12][C:13]([N:15]([CH2:16][C@@:17]1([CH2:26][C:27]([OH:29])=[O:28])[CH2:23][C@H:22]2[C@@H:18]1[CH:19]=[C:20]([CH2:24][CH3:25])[CH2:21]2)[CH3:4])=[O:14])([CH3:9])([CH3:10])[CH3:11]

Participants

6

Reactant 4

HCID 6328Methyl iodideHCID 8028TetrahydrofuranHCID 24758Sodium hydrideHCID 67197694[(1S,5R,6R)-6-{[(tert-butoxycarbonyl)amino]methyl}-3-ethylbicyclo[3.2.0]hept-3-en-6-yl]acetic acid

Product 1

HCID 67200495HCID 67200495, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Sodium hydride (63%, 2.48 g, 65.0 mmol) was added in small portions to a tetrahydrofuran solution (25 mL) of [(1S,5R,6R)-6-{[(tert-butoxycarbonyl)amino]methyl}-3-ethylbicyclo[3.2.0]hept-3-en-6-yl]acetic acid (2.01 g, 6.50 mmol) and methyl iodide (4.05 mL, 65.0 mmol) with stirring at room temperature. The mixture was stirred at this temperature for 6 hours, and water (50 mL) was then added thereto while the reaction solution was cooled on ice, followed by washing with diethyl ether. The aqueous layer was made acidic using 1 M citric acid, followed by extraction with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate. The residue was filtered and concentrated under reduced pressure. Then, the obtained crude product was purified by silica gel column chromatography to obtain the compound of interest as an oil substance (2.00 g, 95%).

Workup

  1. stirringThe mixture was stirred at this temperature for 6 hours
  2. temperaturewhile the reaction solution was cooled on ice
  3. washby washing with diethyl ether
  4. extractionfollowed by extraction with ethyl acetate
  5. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  6. filtrationThe residue was filtered
  7. concentrationconcentrated under reduced pressure
  8. customThen, the obtained crude product
  9. customwas purified by silica gel column chromatography
  10. customto obtain the compound of interest as an oil substance (2.00 g, 95%)

Sources & evidence

ORD record
ord-a4e685df95384412af667ddd03e0ad42
Source dataset
uspto-grants-2011_05
Patent number
US07947738B2

Reaction notes

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