Ethyl Acetate → HCID 68505467, compound

HRID 1715412Notes

Reaction equation

HRID 1715412 reaction equation
CCCC[N+](CCCC)(CCCC)CCCC.[F-].[C:19]([O:23][C:24](=[O:45])[N:25]([CH2:27][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)[CH3:26])([CH3:22])([CH3:21])[CH3:20].CCOC(C)=O>C1COCC1>[C:19]([O:23][C:24](=[O:45])[N:25]([CH2:27][CH2:28][C:29]1[CH:34]=[CH:33][C:32]([Cl:35])=[C:31]([CH2:36][OH:37])[CH:30]=1)[CH3:26])([CH3:22])([CH3:20])[CH3:21]

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 2724141Tetrabutylammonium FluorideHCID 131728335HCID 131728335, compound

Product 1

HCID 68505467HCID 68505467, compoundYield 100.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

TBAF (1M in THF, 2.90 mL, 2.90 mmol) was added to a sol. of {2-[3-(tert-butyl-dimethyl-silanyloxymethyl)-4-chloro-phenyl]-ethyl}-methyl-carbamic acid tert-butyl ester (600 mg, 1.45 mmol) in THF (14.2 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 (435 mg, quantitative yield). LC-MS: tR=0.93 min.

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-46e78a27c71540a0b4d26a8965892793
Source dataset
uspto-grants-2010_09
Patent number
US07799805B2

Reaction notes

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