Methyl iodide → HCID 86714101, compound

HRID 576439Notes

Reaction equation

HRID 576439 reaction equation
[Cl:1][C:2]1[C:10]2[O:9][CH2:8][CH:7]([OH:11])[C:6]=2[C:5]([CH:12]2[C@H:17]([O:18][CH2:19][C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[C@@H:16]([O:26][CH2:27][C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)[C@H:15]([O:34][CH2:35][C:36]3[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=3)[C@@H:14]([CH2:42][O:43][CH2:44][C:45]3[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=3)[O:13]2)=[CH:4][C:3]=1[CH2:51][C:52]1[CH:57]=[CH:56][C:55]([O:58][CH2:59][CH3:60])=[CH:54][CH:53]=1.I[CH3:62].[H-].[Na+]>CN(C=O)C.C([O-])(O)=O.[Na+]>[Cl:1][C:2]1[C:10]2[O:9][CH2:8][CH:7]([O:11][CH3:62])[C:6]=2[C:5]([CH:12]2[C@H:17]([O:18][CH2:19][C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[C@@H:16]([O:26][CH2:27][C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)[C@H:15]([O:34][CH2:35][C:36]3[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=3)[C@@H:14]([CH2:42][O:43][CH2:44][C:45]3[CH:46]=[CH:47][CH:48]=[CH:49][CH:50]=3)[O:13]2)=[CH:4][C:3]=1[CH2:51][C:52]1[CH:57]=[CH:56][C:55]([O:58][CH2:59][CH3:60])=[CH:54][CH:53]=1

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 86714100HCID 86714100, compound

Product 1

HCID 86714101HCID 86714101, compoundYield 90.1%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 516892Sodium BicarbonateSolvent

Procedure

To a mixture solution of 7-chloro-6-(4-ethoxybenzyl)-4-((3S,4R,5R,6R)-3,4,5-tris(benzyloxy)-6-(benzyloxymethyl)-tetrahydro-2H-pyran-2-yl)-2,3-dihydrobenzofuran-3-ol (260 mg, 0.314 mmole) and iodomethane (40 μL, 0.628 mmole) in DMF (10 mL) was added NaH (25.1 mg, 0.628 mmole) at 0° C. The resulting solution was stirred at rt overnight, diluted with sat. NaHCO3 and extracted with ethyl acetate. The organic layer was washed with water then brine, dried over MgSO4, filtered, and concentrated in vacuo. The crude residue was purified on Biotage® purification apparatus to yield the title compound (238 mg, 90%) as a yellow gum.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with water
  3. dry with materialbrine, dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe crude residue was purified on Biotage® purification apparatus

Sources & evidence

ORD record
ord-aba64f3da6624d71b8a7b8c879d71423
Source dataset
uspto-grants-2015_05
Patent number
US09034921B2

Reaction notes

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