Ethyl Acetate → HCID 68508563, compound

HRID 1715405Notes

Reaction equation

HRID 1715405 reaction equation
CCCC[N+](CCCC)(CCCC)CCCC.[F-].[C:19]([O:23][C:24](=[O:47])[N:25]([CH2:30][C:31]1[CH:36]=[CH:35][C:34]([Cl:37])=[C:33]([C:38](C)(C)[O:39][SiH2]C(C)(C)C)[CH:32]=1)[CH2:26][CH:27]1[CH2:29][CH2:28]1)([CH3:22])([CH3:21])[CH3:20].CCOC(C)=O>C1COCC1>[C:19]([O:23][C:24](=[O:47])[N:25]([CH2:30][C:31]1[CH:36]=[CH:35][C:34]([Cl:37])=[C:33]([CH2:38][OH:39])[CH:32]=1)[CH2:26][CH:27]1[CH2:29][CH2:28]1)([CH3:22])([CH3:20])[CH3:21]

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 2724141Tetrabutylammonium FluorideHCID 131728334HCID 131728334, compound

Product 1

HCID 68508563HCID 68508563, compoundYield 44%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

TBAF (1M in THF, 14.0 mL, 14.0 mmol) was added to a sol. of [3-(tert-butyl-dimethyl-silanyloxymethyl)-4-chloro-benzyl]-cyclopropylmethyl-carbamic acid tert-butyl ester (3.08 g, 7.00 mmol) in THF (68 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→CH2Cl2/MeOH 9:1) yielded the title compound (1.00 g, 44%). LC-MS: tR=0.99 min; ES+: 326.10.

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→CH2Cl2/MeOH 9:1)

Sources & evidence

ORD record
ord-56b98d9d72734717a7e135a665564e72
Source dataset
uspto-grants-2010_09
Patent number
US07799805B2

Reaction notes

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