tetrahydrofuran N,N-dimethylformamide → HCID 87087541, compound

HRID 1931095Notes

Reaction equation

HRID 1931095 reaction equation
[C:1]([C:5]1[S:9][C:8]([NH:10][C:11](=[O:17])[O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[N:7][N:6]=1)([CH3:4])([CH3:3])[CH3:2].[CH3:18][C:19]([O-:22])(C)[CH3:20].[K+].[CH2:24]1COC[CH2:25]1.CN(C=O)C>CCOCC>[C:1]([C:5]1[S:9]/[C:8](=[N:10]\[C:11](=[O:17])[O:12][C:13]([CH3:16])([CH3:15])[CH3:14])/[N:7]([CH2:18][C@H:19]2[CH2:20][CH2:25][CH2:24][O:22]2)[N:6]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 21974620tetrahydrofuran N,N-dimethylformamideHCID 23665647Potassium tert-butoxideHCID 66643088HCID 66643088, compound

Product 1

HCID 87087541HCID 87087541, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
75 °C

Procedure

To a mixture of Example 69A (20.0 g, 78.0 mmol) and Example 39A (21.9 g, 85.0 mmol) in THF/DMF (4/1) was added potassium 2-methylpropan-2-olate (13.1 g, 117 mmol). The mixture was heated at 75° C. for 16 hours then cooled to room temperature, diluted with ether and washed with aqueous NaHCO3. The organic extract was dried over Na2SO4 and concentrated under reduced pressure. The residue was purified by flash chromatography on SiO2 using an Analogix® Intelliflash280™ (Hexanes:EtOAc, 0 to 50% gradient) to afford the title compound. MS (ESI+) m/z 342 (M+H)+.

Workup

  1. temperaturethen cooled to room temperature
  2. washwashed with aqueous NaHCO3
  3. extractionThe organic extract
  4. dry with materialwas dried over Na2SO4
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by flash chromatography on SiO2 using an Analogix® Intelliflash280™ (Hexanes:EtOAc, 0 to 50% gradient)

Sources & evidence

ORD record
ord-838e4e4bffe24e30a89d7d452777d5c1
Source dataset
uspto-grants-2012_05
Patent number
US08188135B2

Reaction notes

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