Methyl iodide → HCID 59611493, compound

HRID 1471052Notes

Reaction equation

HRID 1471052 reaction equation
[C:1]([O:5][C:6]([NH:8][C@@H:9]([C:13]([OH:16])([CH3:15])[CH3:14])[C:10]([OH:12])=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].[H-].[Na+].I[CH3:20]>C1COCC1>[C:1]([O:5][C:6]([NH:8][C@@H:9]([C:13]([O:16][CH3:20])([CH3:15])[CH3:14])[C:10]([OH:12])=[O:11])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 11075314N-(tert-Butoxycarbonyl)-3-hydroxy-L-valine

Product 1

HCID 59611493HCID 59611493, compoundYield 43%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of Example 203A (363 mg, 1.56 mmol) in THF (7 mL) at 0° C. was added NaH (373 mg, 9.34 mmol) and stirring was continued for 15 min. Iodomethane (0.78 mL, 12.45 mmol) was added and the solution was allowed to warm to room temperature and stirred for 18 h. Solution was quenched with H2O, diluted with EtOAc, washed with H2O, brine, dried (Na2SO4), filtered and solvent removed to give the title compound (165 mg, 0.67 mmol, 43%). MS (ESI) m/z 248 (M+H)+.

Workup

  1. stirringstirred for 18 h
  2. customSolution was quenched with H2O
  3. additiondiluted with EtOAc
  4. washwashed with H2O, brine
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. customsolvent removed

Sources & evidence

ORD record
ord-1b1946b820d746b78f7ee16efcda94c9
Source dataset
uspto-grants-2015_04
Patent number
US09006387B2

Reaction notes

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