tetrahydrofuran N,N-dimethylformamide → HCID 87087541, compound

HRID 452979Notes

Reaction equation

HRID 452979 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](C)([O-:21])[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:21]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 67A (1.88 g, 7.31 mmol) and Example 11A (2.25 g, 8.77 mmol) in THF/DMF (4/1) was added potassium tert-butoxide (1.12 g, 9.50 mmol). The reaction was heated at 75° C. for 16 hours. The mixture was cooled to room temperature and diluted with ether, washed with aq. NaHCO3, dried over MgSO4 and concentrated under reduced pressure. The residue was purified by column chromatography using an Analogix® Intelliflash280™ (SiO2, 0-50% ethyl acetate in hexanes) to give the title compound. MS (ESI+) m/z 342 (M+H)+.

Workup

  1. temperatureThe mixture was cooled to room temperature
  2. washwashed with aq. NaHCO3
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-ec133763bd424b56b9b7f20a8f8a12af
Source dataset
uspto-grants-2013_07
Patent number
US08492371B2

Reaction notes

Loading…