Diethyl Ether → HCID 59267901, compound

HRID 1809448Notes

Reaction equation

HRID 1809448 reaction equation
[C:1]([O-:4])(=[S:3])[CH3:2].[K+].Br[C:7]([CH3:28])([CH3:27])[C:8]([NH:10][C:11]1[O:15][N:14]=[C:13]([C:16]([CH3:26])([CH3:25])[CH2:17][O:18][CH:19]2[CH2:24][CH2:23][CH2:22][CH2:21][O:20]2)[CH:12]=1)=[O:9].C(OCC)C>CN(C=O)C>[CH3:26][C:16]([C:13]1[CH:12]=[C:11]([NH:10][C:8]([C:7]([S:3][C:1](=[O:4])[CH3:2])([CH3:28])[CH3:27])=[O:9])[O:15][N:14]=1)([CH3:25])[CH2:17][O:18][CH:19]1[CH2:24][CH2:23][CH2:22][CH2:21][O:20]1

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 23670855Potassium ethanethioateHCID 59267955HCID 59267955, compound

Product 1

HCID 59267901HCID 59267901, compoundYield 58.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Potassium thioacetate (6.6 g, 58.0 mmol) is added at 0° C. to a solution of 2-bromo-N-{3-[1,1-dimethyl-2-(tetrahydro-pyran-2-yloxy)-ethyl]-isoxazol-5-yl}-2-methyl-propionamide (15.0 g, 38.6 mmol) in DMF (150 mL). After stirring the reaction mixture at room temperature for 12 h, ice water and diethyl ether are added. The two phases are separated, the organic layer is washed with brine, dried over anhydrous Na2SO4, filtered and concentrated under reduced pressure to afford the crude product that is purified by silica gel chromatography to afford 8.7 g of thioacetic acid S-(1-{3-[1,1-dimethyl-2-(tetrahydro-pyran-2-yloxy)-ethyl]-isoxazol-5-ylcarbamoyl}-1-methyl-ethyl)ester as a pale yellow solid. Yield: 58%; m/z 383 [M−H]; 1H NMR (250 MHz, CHLOROFORM-d) δ ppm 1.35 (6H, d, J=8.07 Hz), 1.45-1.88 (12H, m), 2.37 (3H, s), 3.30-3.58 (2H, m), 3.69-3.87 (2H, m), 4.58 (1H, t), 6.35 (1H, s), 9.44 (1H, br. s.).

Workup

  1. customThe two phases are separated
  2. washthe organic layer is washed with brine
  3. dry with materialdried over anhydrous Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customto afford the crude product that
  7. customis purified by silica gel chromatography

Sources & evidence

ORD record
ord-724fa153f81d42e88c0b5c55b5c67193
Source dataset
uspto-grants-2013_01
Patent number
US08362039B2

Reaction notes

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