Acetic Acid → HCID 86714594, compound

HRID 1025934Notes

Reaction equation

HRID 1025934 reaction equation
[F:1][CH2:2][C:3]([NH:7][C:8](=[O:17])[O:9][CH2:10]C1C=CC=CC=1)([CH3:6])CO.[H-].[Na+].CC(O)=O>C1COCC1>[F:1][CH2:2][C:3]1([CH3:6])[CH2:10][O:9][C:8](=[O:17])[NH:7]1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 24758Sodium hydrideHCID 86714592HCID 86714592, compound

Product 1

HCID 86714594HCID 86714594, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of benzyl 1-fluoro-3-hydroxy-2-methylpropan-2-ylcarbamate (562 mg, 2.3 mmol) in THF (29 ml) was cooled to 0° C. and 60% NaH in mineral oil (117 mg, 2.9 mmol) was added. The reaction was warmed to RT over 3 h, and then heated to 50° C. for 16 h. AcOH (200 ul) was added to quench the reaction, and the solution was concentrated in vacuo. The residue was purified by flash chromatography (1% to 12% MeOH in DCM) to afford the title compound as a clear oil (251 mg, 82%). 1H NMR (CDCl3, 400 MHz) δ 1.40 (d, J=2.0 Hz, 3H), 4.08 (dd, J=2.0, 8.8 Hz, 1H), 4.24 (dd, J=9.6, 20.4 Hz, 1H), 4.32-4.40 (m, 2H), 6.61 (s, 1H). 19F NMR (CDCl3, 376 MHz) δ −225.4 (t, J=47 Hz). 13C NMR (CDCl3, 100 MHz) δ 21.7 (d, J=3 Hz), 67.4 (d, J=20 Hz), 72.3 (d, J=4.2 Hz), 86 (d, J=178 Hz), 159.3 (s).

Workup

  1. temperatureheated to 50° C. for 16 h
  2. customto quench
  3. customthe reaction
  4. concentrationthe solution was concentrated in vacuo
  5. customThe residue was purified by flash chromatography (1% to 12% MeOH in DCM)

Sources & evidence

ORD record
ord-808bce37204a447198eea63f64ab461a
Source dataset
uspto-grants-2014_05
Patent number
US08729112B2

Reaction notes

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