Ethyl Acetate → HCID 68505800, compound

HRID 1715433Notes

Reaction equation

HRID 1715433 reaction equation
CCCC[N+](CCCC)(CCCC)CCCC.[F-].[C:19]([O:23][C:24](=[O:45])[N:25]([CH2:28][C:29]1[CH:34]=[CH:33][C:32]([Cl:35])=[C:31]([C:36](C)(C)[O:37][SiH2]C(C)(C)C)[CH:30]=1)[CH2:26][CH3:27])([CH3:22])([CH3:21])[CH3:20].CCOC(C)=O>C1COCC1>[C:19]([O:23][C:24](=[O:45])[N:25]([CH2:28][C:29]1[CH:34]=[CH:33][C:32]([Cl:35])=[C:31]([CH2:36][OH:37])[CH:30]=1)[CH2:26][CH3:27])([CH3:20])([CH3:21])[CH3:22]

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 2724141Tetrabutylammonium FluorideHCID 131728339HCID 131728339, compound

Product 1

HCID 68505800HCID 68505800, compoundYield 66%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

TBAF (1M in THF, 3.03 mL, 3.03 mmol) was added dropwise to a sol. of [3-(tert-butyl-dimethyl-silanyloxymethyl)-4-chloro-benzyl]-ethyl-carbamic acid tert-butyl ester (628 mg, 1.52 mmol) in THF (14.9 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 (MeOH/CH2Cl2 19:1) yielded the title compound (300 mg, 66%). LC-MS: tR=0.98 min; ES+: 300.28.

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 (MeOH/CH2Cl2 19:1)

Sources & evidence

ORD record
ord-4089459f54b1416f840dca166eff821f
Source dataset
uspto-grants-2010_09
Patent number
US07799805B2

Reaction notes

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