Ethyl Acetate → HCID 67461471, compound

HRID 554555Notes

Reaction equation

HRID 554555 reaction equation
Cl[CH:2]([C:49]1[CH:54]=[CH:53][C:52]([CH:55]2[CH2:57][CH2:56]2)=[CH:51][CH:50]=1)[C:3]1[CH:8]=[CH:7][N:6]=[CH:5][C:4]=1[O:9][C@@H:10]1[CH2:15][C@H:14]([CH2:16][O:17][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[C@@H:13]([O:25][CH2:26][C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[C@H:12]([O:33][CH2:34][C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)[C@H:11]1[O:41][CH2:42][C:43]1[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=1.C(OCC)(=O)C>C(Cl)Cl.C(O)(=O)C.[Zn]>[CH:55]1([C:52]2[CH:51]=[CH:50][C:49]([CH2:2][C:3]3[CH:8]=[CH:7][N:6]=[CH:5][C:4]=3[O:9][C@@H:10]3[CH2:15][C@H:14]([CH2:16][O:17][CH2:18][C:19]4[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=4)[C@@H:13]([O:25][CH2:26][C:27]4[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=4)[C@H:12]([O:33][CH2:34][C:35]4[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=4)[C@H:11]3[O:41][CH2:42][C:43]3[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=3)=[CH:54][CH:53]=2)[CH2:56][CH2:57]1

Participants

6

Reactant 2

HCID 8857Ethyl AcetateHCID 67460225HCID 67460225, compound

Product 1

HCID 67461471HCID 67461471, compoundYield 67%

Reagents, catalysts & solvents 3

HCID 23994ZincCatalystHCID 176Acetic AcidSolventHCID 6344DichloromethaneSolvent

Procedure

In a nitrogen stream, zinc (0.14 g, 2.14 mmol) was added to a solution of 4-[chloro-(4-cyclopropylphenyl)-methyl]-3-((1R,2S,3S,4R,5R)-2,3,4-trisbenzyloxy-5-benzyloxymethyl-cyclohexyloxy)pyridine (0.22 g, 0.28 mmol) in methylene chloride (4.1 mL) and acetic acid (12.4 mL), and the mixture solution was stirred at room temperature for 14 hours. To the reaction mixture was added ethyl acetate and the mixture was washed with a saturated hydrogencarbonate 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=ethyl acetate:n-hexane (1:1)] to obtain the title product (0.14 g, 67%).

Workup

  1. washthe mixture was washed with a saturated hydrogencarbonate aqueous solution
  2. dry with materialdried (anhydrous magnesium sulfate)
  3. distillationthe solvent was distilled under reduced pressure
  4. customThe obtained residue was purified by silica gel column chromatography [developing solution=ethyl acetate:n-hexane (1:1)]

Sources & evidence

ORD record
ord-4ee4f4c45e504afe9753c9c299e46cd6
Source dataset
uspto-grants-2011_11
Patent number
US08048897B2

Reaction notes

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