Ethyl Acetate → HCID 66839103, compound

HRID 546686Notes

Reaction equation

HRID 546686 reaction equation
CCCC[N+](CCCC)(CCCC)CCCC.[F-].[Si]([O:36][CH2:37][CH2:38][C@@H:39]([O:61][CH2:62][O:63][CH3:64])[C@H:40]([C:52]1[CH:57]=[C:56]([F:58])[C:55]([F:59])=[C:54]([F:60])[CH:53]=1)[C:41]([NH:43][NH:44][C:45]([O:47][C:48]([CH3:51])([CH3:50])[CH3:49])=[O:46])=[O:42])(C(C)(C)C)(C1C=CC=CC=1)C1C=CC=CC=1.C(OCC)(=O)C.[Cl-].[NH4+]>C1COCC1>[OH:36][CH2:37][CH2:38][C@@H:39]([O:61][CH2:62][O:63][CH3:64])[C@H:40]([C:52]1[CH:57]=[C:56]([F:58])[C:55]([F:59])=[C:54]([F:60])[CH:53]=1)[C:41]([NH:43][NH:44][C:45]([O:47][C:48]([CH3:51])([CH3:50])[CH3:49])=[O:46])=[O:42]

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 25517Ammonium ChlorideHCID 2724141Tetrabutylammonium FluorideHCID 66839342HCID 66839342, compound

Product 1

HCID 66839103HCID 66839103, compoundYield 99.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

TBAF (1.36 mL; 1 M solution in THF) was added to a solution of tert-butyl N′-[(2S*,3R*)-5-(tert-butyldiphenylsilanyloxy)-3-methoxymethoxy-2-(3,4,5-trifluorophenyl)pentanoyl]hydrazinecarboxylate (600 mg) in THF (10 mL). The reaction solution was stirred at room temperature for one hour. Then, ethyl acetate and a saturated ammonium chloride solution were added to the reaction solution, and the organic layer was separated. The resulting organic layer was washed with brine, dried over anhydrous magnesium sulfate and then concentrated under reduced pressure. The residue was purified by silica gel column chromatography (elution solvent: heptane-ethyl acetate system) to obtain 383 mg of the title compound. The property value of the compound is as follows.

Workup

  1. customthe organic layer was separated
  2. washThe resulting organic layer was washed with brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (elution solvent: heptane-ethyl acetate system)

Sources & evidence

ORD record
ord-8d171249e6674678b2bff409dc7b2ce2
Source dataset
uspto-grants-2011_05
Patent number
US07935815B2

Reaction notes

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