Methyl iodide → HCID 16109134, compound

HRID 731534Notes

Reaction equation

HRID 731534 reaction equation
[F:1][C:2]1[CH:26]=[CH:25][CH:24]=[CH:23][C:3]=1[CH2:4][C:5]1([OH:22])[CH2:10][CH2:9][N:8]([C:11]2[CH:21]=[CH:20][C:14]([C:15]([O:17][CH2:18][CH3:19])=[O:16])=[CH:13][CH:12]=2)[CH2:7][CH2:6]1.[H-].[Na+].[CH3:29]I>C1COCC1.CN(P(N(C)C)(N(C)C)=O)C>[F:1][C:2]1[CH:26]=[CH:25][CH:24]=[CH:23][C:3]=1[CH2:4][C:5]1([O:22][CH3:29])[CH2:6][CH2:7][N:8]([C:11]2[CH:21]=[CH:20][C:14]([C:15]([O:17][CH2:18][CH3:19])=[O:16])=[CH:13][CH:12]=2)[CH2:9][CH2:10]1

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 16109051HCID 16109051, compound

Product 1

HCID 16109134HCID 16109134, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 12679HexamethylphosphoramideSolvent

Procedure

A solution of EXAMPLE 1C (17.89 g, 50.1 mmol) in THF (150 mL) and HMPA (33 mL) was treated with NaH (4.0 g of a 60% dispersion, 100 mmol) at 0° C., stirred for 30 minutes, treated with CH3I (20 mL, 321 mmol), and stirred overnight. The reaction mixture was partitioned between ethyl acetate and saturated aqueous NH4Cl. The organic layer was washed with water (2×), dried (MgSO4), and filtered. Filtration of the concentrate provided the desired product which was used without further purification. MS (ESI) m/e 372 (M+H)+.

Workup

  1. stirringstirred overnight
  2. customThe reaction mixture was partitioned between ethyl acetate and saturated aqueous NH4Cl
  3. washThe organic layer was washed with water (2×)
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. filtrationFiltration of the concentrate

Sources & evidence

ORD record
ord-1433d2e4c77c4d5896ca3cea066dc8ca
Source dataset
uspto-grants-2009_09
Patent number
US07585858B2

Reaction notes

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