Methyl iodide → HCID 86596095, compound

HRID 2222439Notes

Reaction equation

HRID 2222439 reaction equation
[C:1]([O:5][C:6]([NH:8][CH2:9][C:10]1[CH:11]=[C:12]([CH:16]([OH:26])[C:17]2([C:22]([O:24][CH3:25])=[O:23])[CH2:21][CH2:20][CH2:19][O:18]2)[CH:13]=[CH:14][CH:15]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[H-].[Na+].[CH3:29]I.[Cl-].[NH4+].[C:33](=[S:35])=[S:34]>O1CCCC1.C(OCC)(=O)C>[C:1]([O:5][C:6]([NH:8][CH2:9][C:10]1[CH:11]=[C:12]([CH:16]([O:26][C:33]([S:35][CH3:29])=[S:34])[C:17]2([C:22]([O:24][CH3:25])=[O:23])[CH2:21][CH2:20][CH2:19][O:18]2)[CH:13]=[CH:14][CH:15]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

8

Reactant 5

HCID 6328Methyl iodideHCID 6348Carbon DisulfideHCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 59712469HCID 59712469, compound

Product 1

HCID 86596095HCID 86596095, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 2.48 g of methyl 2-[(3-{[(t-butoxycarbonyl)amino]methyl}-phenyl)(hydroxy)methyl]-tetrahydro-2-furancarboxylate in 100 ml of tetrahydrofuran was added sodium hydride (60% in oil) at 0° C. under an atmosphere of nitrogen gas. After stirring at room temperature for 15 minutes, the mixture was cooled to 0° C., and 0.62 ml of carbon disulfide and 0.64 ml of methyl iodide were added. After stirring at room temperature overnight, 200 ml of ethyl acetate and 50 ml of saturated aqueous ammonium chloride were added. The organic layer was dried over magnesium sulfate and evaporated. The residue was purified by silica gel column chromatography, to give 2.02 g of the title compound as a yellow oil.

Workup

  1. temperaturethe mixture was cooled to 0° C.
  2. stirringAfter stirring at room temperature overnight
  3. dry with materialThe organic layer was dried over magnesium sulfate
  4. customevaporated
  5. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-9e8178363b8a449f9257b8b52e25c3e3
Source dataset
uspto-grants-2008_05
Patent number
US07371777B2

Reaction notes

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