Methyl iodide → HCID 58109721, compound

HRID 2037488Notes

Reaction equation

HRID 2037488 reaction equation
[Si:1]([O:8][CH2:9][CH2:10][CH2:11][C@@:12]1([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[O:17][C:16](=[O:18])[N:15]([C@H:19]([C:21]2[CH:26]=[CH:25][C:24]([CH2:27][OH:28])=[CH:23][CH:22]=2)[CH3:20])[CH2:14][CH2:13]1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[H-].[Na+].[CH3:37]I>C1COCC1>[Si:1]([O:8][CH2:9][CH2:10][CH2:11][C@@:12]1([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[O:17][C:16](=[O:18])[N:15]([C@H:19]([C:21]2[CH:22]=[CH:23][C:24]([CH2:27][O:28][CH3:37])=[CH:25][CH:26]=2)[CH3:20])[CH2:14][CH2:13]1)([C:4]([CH3:5])([CH3:6])[CH3:7])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 58109689HCID 58109689, compound

Product 1

HCID 58109721HCID 58109721, compoundYield 100.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (R)-6-(3-(tert-butyldimethylsilyloxy)propyl)-3-((S)-1-(4-(hydroxymethyl)phenyl)ethyl)-6-phenyl-1,3-oxazinan-2-one (10 mg, 0.02 mmol) in THF (5 mL) was added NaH (1.4 mg) at 0° C. After stirring for 1 h at rt, the mixture was cooled to 0° C., and CH3I (90 mg 0.78 mmol) was added. The mixture was stirred overnight at rt. The reaction was quenched with H2O, and the layers were separated. The aqueous layer was extracted with CH2Cl2 for two times. The organic layer was combined, washed with brine, dried over Na2SO4 and concentrated to give the crude product, which was purified by preparative TLC to give (R)-6-(3-(tert-butyldimethylsilyloxy)propyl)-3-((S)-1-(4-(methoxymethyl)phenyl)ethyl)-6-phenyl-1,3-oxazinan-2-one (10 mg, 71%).

Workup

  1. temperaturethe mixture was cooled to 0° C.
  2. stirringThe mixture was stirred overnight at rt
  3. customThe reaction was quenched with H2O
  4. customthe layers were separated
  5. extractionThe aqueous layer was extracted with CH2Cl2 for two times
  6. washwashed with brine
  7. dry with materialdried over Na2SO4
  8. concentrationconcentrated
  9. customto give the crude product, which
  10. customwas purified by preparative TLC

Sources & evidence

ORD record
ord-07d3a04a0d1f4cb4a3238b993e0cc630
Source dataset
uspto-grants-2013_11
Patent number
US08575156B2

Reaction notes

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