Ethyl Acetate → HCID 86622964, compound

HRID 1715430Notes

Reaction equation

HRID 1715430 reaction equation
CCCC[N+](CCCC)(CCCC)CCCC.[F-].[C:19]([O:23][C:24](=[O:46])[N:25]([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][CH2:27][F:28])([CH3:22])([CH3:21])[CH3:20].CCOC(C)=O>C1COCC1>[C:19]([O:23][C:24](=[O:46])[N:25]([CH2:29][C:30]1[CH:35]=[CH:34][C:33]([Cl:36])=[C:32]([CH2:37][OH:38])[CH:31]=1)[CH2:26][CH2:27][F:28])([CH3:22])([CH3:20])[CH3:21]

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 2724141Tetrabutylammonium FluorideHCID 131728338HCID 131728338, compound

Product 1

HCID 86622964HCID 86622964, compoundYield 64.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

TBAF (1M in THF, 8.84 mL, 8.84 mmol) was added to a sol. of [3-(tert-butyl-dimethyl-silanyloxymethyl)-4-chloro-benzyl]-(2-fluoro-ethyl)-carbamic acid tert-butyl ester (1.91 g, 4.42 mmol) in THF (44.2 mL) at 0° C. The mixture was stirred for 1 h while warming up to rt. EtOAc (100 mL) was added, and the resulting mixture was washed with aq. sat. NH4Cl (2×) and brine (1×). The org. layer was dried over MgSO4, filtered, and the solvents were removed under reduced pressure. Purification of the crude by FC (EtOAc/heptane 30:70) yielded the title compound (901 mg, 64%). LC-MS: tR=0.64 min; ES+: 318.07.

Workup

  1. washthe resulting mixture was washed with aq. sat. NH4Cl (2×) and brine (1×)
  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 (EtOAc/heptane 30:70)

Sources & evidence

ORD record
ord-9dfedc357b7a493d9f94437396326ba6
Source dataset
uspto-grants-2010_09
Patent number
US07799805B2

Reaction notes

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