Methyl iodide → HCID 86608495, compound

HRID 1432036Notes

Reaction equation

HRID 1432036 reaction equation
[C:1]([O:5][C:6](=[O:22])[CH2:7][NH:8][CH:9]([C:13](C)(C)[O:14][SiH2]C(C)(C)C)[CH:10]([CH3:12])[CH3:11])([CH3:4])([CH3:3])[CH3:2].[CH:23](N(C(C)C)CC)(C)C.CI>CN(C=O)C>[C:1]([O:5][C:6](=[O:22])[CH2:7][N:8]([CH:9]([CH2:13][OH:14])[CH:10]([CH3:11])[CH3:12])[CH3:23])([CH3:2])([CH3:3])[CH3:4]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 81531DiisopropylethylamineHCID 131727714HCID 131727714, compound

Product 1

HCID 86608495HCID 86608495, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

{[1-(tert-Butyl-dimethyl-silanyloxymethyl)-2-methyl-propyl]-amino}-acetic acid tert-butyl ester (1.9 g, 6.1 mmol) and diisopropylethylamine (4.2 mL, 24 mmol) were dissolved in DMF (15 mL). A solution of MeI (0.45 mL, 7.3 mmol) in DMF (100 mL) was slowly added over 15 min. The reaction was stirred for 2½ h. The solvent was removed in vacuo. The residue product was dissolved in EtOAc (100 mL) and the solution was washed with water (20 mL). The organic phase was dried over magnesium sulfate, filtered and the filtrate was evaporated in vacuo. The residue was dissolved in acetonitrile (45 mL) and Et3N 3HF (2 mL, 12.3 mmol) was added. The reaction was stirred for 16 h. The solvent was removed in vacuo. The crude product was dissolved in EtOAc (100 mL) and washed with saturated sodium bicarbonate solution (25 mL) and saturated sodium chloride solution (25 mL). The organic phase was dried over magnesium sulfate and the solution was slowly filtered through 5 g of silica gel. The filtrate was evaporated in vacuo. Yield: 1.1 g, 78%.

Workup

  1. customThe solvent was removed in vacuo
  2. dissolutionThe residue product was dissolved in EtOAc (100 mL)
  3. washthe solution was washed with water (20 mL)
  4. dry with materialThe organic phase was dried over magnesium sulfate
  5. filtrationfiltered
  6. customthe filtrate was evaporated in vacuo
  7. dissolutionThe residue was dissolved in acetonitrile (45 mL)
  8. additionEt3N 3HF (2 mL, 12.3 mmol) was added
  9. stirringThe reaction was stirred for 16 h
  10. customThe solvent was removed in vacuo
  11. dissolutionThe crude product was dissolved in EtOAc (100 mL)
  12. washwashed with saturated sodium bicarbonate solution (25 mL) and saturated sodium chloride solution (25 mL)
  13. dry with materialThe organic phase was dried over magnesium sulfate
  14. filtrationthe solution was slowly filtered through 5 g of silica gel
  15. customThe filtrate was evaporated in vacuo

Sources & evidence

ORD record
ord-3dafd75e05bc474d8ed618001091a4a5
Source dataset
uspto-grants-2009_11
Patent number
US07612068B2

Reaction notes

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