Ethyl Acetate → HCID 68506145, compound

HRID 1715415Notes

Reaction equation

HRID 1715415 reaction equation
CCCC[N+](CCCC)(CCCC)CCCC.[F-].[C:19]([O:23][C:24](=[O:44])[N:25]([CH2:27][C:28]1[CH:33]=[CH:32][C:31]([Cl:34])=[C:30]([C:35](C)(C)[O:36][SiH2]C(C)(C)C)[CH:29]=1)[CH3:26])([CH3:22])([CH3:21])[CH3:20].CCOC(C)=O>C1COCC1>[C:19]([O:23][C:24](=[O:44])[N:25]([CH2:27][C:28]1[CH:33]=[CH:32][C:31]([Cl:34])=[C:30]([CH2:35][OH:36])[CH:29]=1)[CH3:26])([CH3:22])([CH3:20])[CH3:21]

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 2724141Tetrabutylammonium FluorideHCID 131728336HCID 131728336, compound

Product 1

HCID 68506145HCID 68506145, compoundYield 34.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

TBAF (1M in THF, 2.25 mL, 2.25 mmol) was added to a sol. of [3-(tert-butyl-dimethyl-silanyloxymethyl)-4-chloro-benzyl]-methyl-carbamic acid tert-butyl ester (450 mg, 1.13 mmol) in THF (11 mL) at 0° C. The mixture was stirred for 1 h while warming up to rt. EtOAc (50 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 40:60) yielded the title compound (110 mg, 34%). LC-MS: tR=0.91 min; ES+: 271.10.

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 40:60)

Sources & evidence

ORD record
ord-e4c66396e2c2404daf70dcfee91c7660
Source dataset
uspto-grants-2010_09
Patent number
US07799805B2

Reaction notes

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