Methyl iodide → HCID 86664970, compound

HRID 1188019Notes

Reaction equation

HRID 1188019 reaction equation
O1CCC[CH2:2]1.[C:6]([O:9][N:10]([C:17]([O:19][C:20]([CH3:30])([CH3:29])[CH2:21][CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)=[O:18])[CH2:11][CH2:12][O:13][CH2:14][CH2:15][OH:16])(=[O:8])[CH3:7].[H-].[Na+].IC>O>[C:6]([O:9][N:10]([C:17]([O:19][C:20]([CH3:30])([CH3:29])[CH2:21][CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)=[O:18])[CH2:11][CH2:12][O:13][CH2:14][CH2:15][O:16][CH3:2])(=[O:8])[CH3:7]

Participants

6

Reactant 4

HCID 6328Methyl iodideHCID 8028Tetrahydrofuran2×HCID 24758Sodium hydrideHCID 86664971HCID 86664971, compound

Product 1

HCID 86664970HCID 86664970, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Under an argon gas atmosphere, a tetrahydrofuran (20 mL) solution of benzyl{tert-butoxycarbonyl-[2-(2-hydroxyethoxy)ethyl]amino} acetate (5.83 g, 16.5 mmol) was added dropwise to a tetrahydrofuran (10 mL) solution of sodium hydride (1.2 g, 24.8 mmol, 50% in mineral oil) at 0° C. After stirring at the same temperature for 20 minutes, iodomethane (1.6 mL, 24.8 mmol) was added at 0° C. The reaction mixed liquid was stirred at room temperature for 20 hours and then water was added while cooling in an ice bath, thereby terminating the reaction. The reaction liquid was extracted three times with ether and the organic layer was dried, and then the residue was concentrated under reduced pressure and purified by silica gel flash column chromatography (eluent: hexane/ethyl acetate=5/1, 3/1) to obtain benzyl{tert-butoxycarbonyl-[2-(2-methoxyethoxy)ethyl]amino} acetate (3.02 g, 8.21 mmol) as a colorless oily product with a yield of 50%.

Workup

  1. additionThe reaction mixed liquid
  2. stirringwas stirred at room temperature for 20 hours
  3. temperaturewhile cooling in an ice bath
  4. customterminating
  5. customthe reaction
  6. customThe reaction liquid
  7. extractionwas extracted three times with ether
  8. customthe organic layer was dried
  9. concentrationthe residue was concentrated under reduced pressure
  10. custompurified by silica gel flash column chromatography (eluent: hexane/ethyl acetate=5/1, 3/1)

Sources & evidence

ORD record
ord-8bebcf8107294661965a4a1f3d5f5d74
Source dataset
uspto-grants-2014_03
Patent number
US08673958B2

Reaction notes

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