tetrahydrofuran N,N-dimethylformamide → HCID 87087541, compound

HRID 536731Notes

Reaction equation

HRID 536731 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-86fa5d56170f4f249ee7377cd8f74b25
Source dataset
uspto-grants-2014_10
Patent number
US08859596B2

Reaction notes

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