Water → HCID 11646899, compound

HRID 554577Notes

Reaction equation

HRID 554577 reaction equation
CSC.[CH2:4]([C:6]1[CH:60]=[CH:59][C:9]([CH2:10][N:11]2[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[C:13]([C@@H:20]3[CH2:25][C@H:24]([CH2:26][O:27]CC4C=CC=CC=4)[C@@H:23]([O:35]CC4C=CC=CC=4)[C@H:22]([O:43]CC4C=CC=CC=4)[C@H:21]3[O:51]CC3C=CC=CC=3)=[CH:12]2)=[CH:8][CH:7]=1)[CH3:5].O>C(Cl)Cl>[CH2:4]([C:6]1[CH:60]=[CH:59][C:9]([CH2:10][N:11]2[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[C:13]([C@@H:20]3[CH2:25][C@H:24]([CH2:26][OH:27])[C@@H:23]([OH:35])[C@H:22]([OH:43])[C@H:21]3[OH:51])=[CH:12]2)=[CH:8][CH:7]=1)[CH3:5]

Participants

5

Reactant 3

HCID 962WaterHCID 1068Dimethyl SulfideHCID 67458539HCID 67458539, compound

Product 1

HCID 11646899HCID 11646899, compoundYield 41%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

In a nitrogen stream, dimethylsulfide (0.72 mL) and a boron trifluoride-diethyl ether complex (0.36 mL, 2.8 mmol) were added to a solution of 1-(4-ethylbenzyl)-3-[(1S,2S,3R, 4R,5R)-2,3,4-tris-benzyloxy-5-(benzyloxymethyl)cyclohexyl]-1H-indole (213 mg, 2.28 mmol) in methylene chloride (4.7 mL) under cooling with ice. The mixture solution was stirred at room temperature for 64 hours, and then water was added thereto under cooling with ice and the resulting solution was extracted with methylene chloride. The organic layer was washed with a saturated sodium chloride aqueous solution and dried (anhydrous magnesium sulfate) and then the solvent was distilled under reduced pressure. The obtained residue was purified by silica gel column chromatography [developing solution=methylene chloride:methanol (50:1)] to obtain the title compound (45 mg, 41%).

Workup

  1. temperatureunder cooling with ice
  2. temperatureunder cooling with ice
  3. extractionthe resulting solution was extracted with methylene chloride
  4. washThe organic layer was washed with a saturated sodium chloride aqueous solution
  5. dry with materialdried (anhydrous magnesium sulfate)
  6. distillationthe solvent was distilled under reduced pressure
  7. customThe obtained residue was purified by silica gel column chromatography [developing solution=methylene chloride:methanol (50:1)]

Sources & evidence

ORD record
ord-4d3142ac1fd946c4bdd1a4631695ef7b
Source dataset
uspto-grants-2011_11
Patent number
US08048897B2

Reaction notes

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