Acetic Acid → HCID 86714598, compound

HRID 1025939Notes

Reaction equation

HRID 1025939 reaction equation
[F:1][C:2]([F:20])([F:19])[CH2:3][C:4]([NH:8][C:9](=[O:18])[O:10][CH2:11]C1C=CC=CC=1)([CH3:7])CO.[H-].[Na+].CC(O)=O>C1COCC1>[CH3:7][C:4]1([CH2:3][C:2]([F:1])([F:19])[F:20])[CH2:11][O:10][C:9](=[O:18])[NH:8]1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 24758Sodium hydrideHCID 86714597HCID 86714597, compound

Product 1

HCID 86714598HCID 86714598, compoundYield 77.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of benzyl 4,4,4-trifluoro-1-hydroxy-2-methylbutan-2-ylcarbamate (830 mg, 2.85 mmol) in THF (55 ml) was cooled to 0° C., and 60% NaH in mineral oil (143 mg, 3.6 mmol) added in one portion. The suspension was stirred for 30 min, then warmed to RT and stirred for 24 h. AcOH (200 ul) added to quench the reaction, and the solution was concentrated in vacuo. The residue was purified by flash chromatography (5% to 20% CH3CN in DCM) to afford the title compound as a white solid (405 mg). 1H NMR (CDCl3, 400 MHz) δ 1.47 (s, 3H), 2.43-2.53 (m, 2H), 4.10 (d, J=8.8 Hz, 1H), 4.28 (d, J=8.8 Hz, 1H), 6.84 (s, 1H). 19F NMR (CDCl3, 376 MHz) δ −61.3 (t, J=10.9 Hz). 13C NMR (CDCl3, 100 MHz) δ 25.3, 43.0 (q, J=27.2 Hz), 55.0, 75.4, 125 (q, J=277.8 Hz), 158.7. LRMS (ESI/APCI): 184 [M+H]+, 225 [M+H+CH3CN]+.

Workup

  1. stirringstirred for 24 h
  2. customto quench
  3. customthe reaction
  4. concentrationthe solution was concentrated in vacuo
  5. customThe residue was purified by flash chromatography (5% to 20% CH3CN in DCM)

Sources & evidence

ORD record
ord-5ef1b0ab9aea47fa95057153421bb7ed
Source dataset
uspto-grants-2014_05
Patent number
US08729112B2

Reaction notes

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