Methyl iodide → HCID 90295754, compound

HRID 1050217Notes

Reaction equation

HRID 1050217 reaction equation
[Si:1]([O:8][CH2:9][C@H:10]1[C@H:18]2[N:13]([C:14]3[CH:22]=[CH:21][C:20]([NH:23][C:24](=[O:26])[CH3:25])=[CH:19][C:15]=3[O:16][CH2:17]2)[C:12](=[O:27])[O:11]1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[H-].[Na+].IC.[CH3:32]C(=O)OCC>C1COCC1>[Si:1]([O:8][CH2:9][C@H:10]1[C@H:18]2[N:13]([C:14]3[CH:22]=[CH:21][C:20]([N:23]([CH3:32])[C:24](=[O:26])[CH3:25])=[CH:19][C:15]=3[O:16][CH2:17]2)[C:12](=[O:27])[O:11]1)([C:4]([CH3:7])([CH3:5])[CH3:6])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 6328Methyl iodideHCID 8857Ethyl AcetateHCID 24758Sodium hydrideHCID 90295631HCID 90295631, compound

Product 1

HCID 90295754HCID 90295754, compoundYield 87.11%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Compound N-((3R,3aS)-3-(((t-butyldimethylsilyl)oxy)methyl)-1-oxo-1,3,3a,4-tetrahydrobenzo[b]oxazolo[3,4-d][1,4]oxazin-7-yl)-acetamide (0.685 g, 1.747 mmol) was dissolved in 20 ml of THF and cooled on ice-salt bath. 60% NaH (0.14 g, 3.495 mmol) was added. The ice bath was removed, and the reaction mixture was stirred at room temperature for 30 min, and then cooled on ice-salt bath. Iodomethane (0.496 g, 3.495 mmol) was added slowly in dropwise. The ice bath was removed, and the reaction mixture was stirred at room temperature for 3 h. TLC (PE/EA=1/1) was employed to monitor the reaction. After the reaction completed, the reaction was quenched by adding 10 ml of water and then extracted with EA (10 ml×3). The organic phase was combined, dried over anhydrous sodium sulfate, and the solvent was evaporated. Column chromatography (PE/EA=3/1) afforded white solid 0.618 g, yield: 87.11%.

Workup

  1. temperaturecooled on ice-salt bath
  2. customThe ice bath was removed
  3. temperaturecooled on ice-salt bath
  4. customThe ice bath was removed
  5. stirringthe reaction mixture was stirred at room temperature for 3 h
  6. customthe reaction
  7. customthe reaction was quenched
  8. additionby adding 10 ml of water
  9. extractionextracted with EA (10 ml×3)
  10. dry with materialdried over anhydrous sodium sulfate
  11. customthe solvent was evaporated

Sources & evidence

ORD record
ord-a7be4e85affe49a8bff444f59a10fff6
Source dataset
uspto-grants-2016_07
Patent number
US09382265B2

Reaction notes

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