Ethyl Acetate → HCID 68504289, compound

HRID 1715423Notes

Reaction equation

HRID 1715423 reaction equation
CCCC[N+](CCCC)(CCCC)CCCC.[F-].[C:19]([O:23][C:24](=[O:46])[N:25]([CH2:28][CH2:29][C:30]1[CH:35]=[CH:34][C:33]([Cl:36])=[C:32]([C:37](C)(C)[O:38][SiH2]C(C)(C)C)[CH:31]=1)[CH2:26][CH3:27])([CH3:22])([CH3:21])[CH3:20].CCOC(C)=O>C1COCC1>[C:19]([O:23][C:24](=[O:46])[N:25]([CH2:28][CH2:29][C:30]1[CH:35]=[CH:34][C:33]([Cl:36])=[C:32]([CH2:37][OH:38])[CH:31]=1)[CH2:26][CH3:27])([CH3:20])([CH3:21])[CH3:22]

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 2724141Tetrabutylammonium FluorideHCID 131728337HCID 131728337, compound

Product 1

HCID 68504289HCID 68504289, compoundYield 50.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

TBAF (1M in THF, 1.39 mL, 1.39 mmol) was added to a sol. of {2-[3-(tert-butyl-dimethyl-silanyloxymethyl)-4-chloro-phenyl]-ethyl}-ethyl-carbamic acid tert-butyl ester (298 mg, 0.696 mmol) in THF (6.82 mL) at 0° C. The mixture was stirred for 1 h while warming up to rt. EtOAc was added, and the mixture was washed with aq. sat. NH4Cl and brine. The org. layer was dried over MgSO4, filtered, and the solvents were removed under reduced pressure. Purification of the crude by FC (CH2Cl2/MeOH 19:1) yielded the title compound (110 mg, 50%). LC-MS: tR=0.97 min; ES+: 314.11.

Workup

  1. washthe mixture was washed with aq. sat. NH4Cl and brine
  2. dry with materiallayer was dried over MgSO4
  3. filtrationfiltered
  4. customthe solvents were removed under reduced pressure
  5. customPurification of the crude by FC (CH2Cl2/MeOH 19:1)

Sources & evidence

ORD record
ord-1b44916017534a329e81fdd504c126bb
Source dataset
uspto-grants-2010_09
Patent number
US07799805B2

Reaction notes

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