Methyl iodide → HCID 59557691, compound

HRID 1175306Notes

Reaction equation

HRID 1175306 reaction equation
[H-].[Na+].[Cl:3][C:4]1[C:5]([CH2:54][C:55]2[CH:60]=[CH:59][C:58]([CH2:61][CH3:62])=[CH:57][CH:56]=2)=[CH:6][C:7]([C@H:15]2[C@H:20]([O:21][CH2:22][C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)[C@@H:19]([O:29][CH2:30][C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=3)[C@H:18]([O:37][CH2:38][C:39]3[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=3)[C@@H:17]([CH2:45][O:46][CH2:47][C:48]3[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=3)[O:16]2)=[C:8]([CH:14]=1)[CH2:9][O:10][CH2:11][CH2:12][OH:13].[CH3:63]I>C1COCC1.CCCC[N+](CCCC)(CCCC)CCCC.[I-]>[CH2:38]([O:37][C@H:18]1[C@H:19]([O:29][CH2:30][C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[C@@H:20]([O:21][CH2:22][C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=2)[C@H:15]([C:7]2[CH:6]=[C:5]([CH2:54][C:55]3[CH:60]=[CH:59][C:58]([CH2:61][CH3:62])=[CH:57][CH:56]=3)[C:4]([Cl:3])=[CH:14][C:8]=2[CH2:9][O:10][CH2:11][CH2:12][O:13][CH3:63])[O:16][C@@H:17]1[CH2:45][O:46][CH2:47][C:48]1[CH:49]=[CH:50][CH:51]=[CH:52][CH:53]=1)[C:39]1[CH:40]=[CH:41][CH:42]=[CH:43][CH:44]=1

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 59557726HCID 59557726, compound

Product 1

HCID 59557691HCID 59557691, compound

Reagents, catalysts & solvents 2

HCID 67553Tetrabutylammonium IodideCatalystHCID 8028TetrahydrofuranSolvent

Procedure

NaH (2 mg, 0.087 mmol) was added to a solution of 2-(5-chloro-4-(4-ethylbenzyl)-2-((2S,3S,4R,5R,6R)-3,4,5-tris(benzyloxy)-6-(benzyloxymethyl)tetrahydro-2H-pyran-2-yl)benzyloxy)ethanol (intermediate O-3) (60 mg, 0.073 mmol) in anhydrous THF (10 mL) at 0° C., and stirred for 1 h, then TBAI (2.6 mg, 0.007 mmol) and CH3I (1.5 mg, 0.11 mmol) were added to the reaction mixture at the same temperature and stirred overnight. Then the mixture was washed with water (10 mL×3), then brine, and the organic layer was dried over Na2SO4, filtered, and evaporated to dryness. The residue (intermediate S-1) was used in the next step without further purification.

Workup

  1. stirringstirred overnight
  2. washThen the mixture was washed with water (10 mL×3)
  3. dry with materialbrine, and the organic layer was dried over Na2SO4
  4. filtrationfiltered
  5. customevaporated to dryness
  6. customThe residue (intermediate S-1) was used in the next step without further purification

Sources & evidence

ORD record
ord-8f5188ebd18345e49a4c1beb71510b1f
Source dataset
uspto-grants-2010_11
Patent number
US07838498B2

Reaction notes

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