Dimethylformamide → HCID 68774716, compound

HRID 1176953Notes

Reaction equation

HRID 1176953 reaction equation
[CH2:1]([O:13][C:14]1[CH:15]=[C:16]([C:33](=[O:43])[C:34]([C:36]2[CH:41]=[CH:40][C:39]([OH:42])=[CH:38][CH:37]=2)=[O:35])[CH:17]=[CH:18][C:19]=1[O:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH3:32])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12].[C:44]([O-:47])([O-])=O.[K+].[K+].CN([CH:53]=[O:54])C>>[CH2:1]([O:13][C:14]1[CH:15]=[C:16]([C:33](=[O:43])[C:34]([C:36]2[CH:37]=[CH:38][C:39]([O:42][CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][O:54][CH2:53][C:8]3([CH3:9])[CH2:44][O:47][CH2:7]3)=[CH:40][CH:41]=2)=[O:35])[CH:17]=[CH:18][C:19]=1[O:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH3:32])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12]

Participants

4

Reactant 3

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 59560833HCID 59560833, compound

Product 1

HCID 68774716HCID 68774716, compoundYield 52%

Conditions

Temperature
80 °C

Procedure

A mixture of JYC-I-146-A (1.46 g, 2.5 mmol), JYC-I-43-A (0.72 g, 2.7 mmol), and K2CO3 (0.68 g, 4.9 mmol) in 30 mL of DMF was refluxed at 80° C. overnight and then heated at 150° C. for additional 3 h. The reaction mixture was quenched with a saturated NH4Cl aqueous solution and extracted with CH2Cl2. The organic phase was washed with H2O and dried over anhydrous MgSO4. The solvent was removed under reduced pressure to give brown oil. The crude product was purified by column chromatography (silica gel, hexanes:ethyl acetate=6:1 (v/v)) to give a yellow solid (0.99 g, 52%). 1H NMR (300 MHz, CDCl3, δ): 7.89 (d, J=8.8 Hz, 2H), 7.54 (d, J=2.0 Hz, 1H), 7.41 (dd, J=8.3 Hz, 2.0 Hz, 1H), 6.91 (d, J=9.3 Hz, 2H), 6.82 (d, J=8.8 Hz, 1H), 4.47 (d, J=5.9 Hz, 2H), 4.32 (d, J=5.9 Hz, 2H), 3.98-4.05 (m, 6H), 3.443 (t, J=6.3 Hz, 2H), 3.437 (s, 2H), 1.80 (m, 6H), 1.59 (m, 2H), 1.27 (s, 3H), 1.20-1.50 (m, 40H), 0.85 (t, J=6.6 Hz, 6H). 13C {1H} NMR (75 MHz, CDCl3, δ): 193.73, 193.45, 164.35, 154.99, 149.30, 132.28, 126.19, 126.08, 126.03, 114.61, 112.31, 111.60, 80.13, 76.04, 71.36, 69.20, 69.07, 68.26, 39.88, 31.86, 29.65, 29.61, 29.57, 29.54, 29.41, 29.30, 29.03, 28.93, 28.88, 25.94, 25.87, 25.74, 22.63, 21.32, 14.05. HRMS-FAB (m/z): [M]+ calcd for C49H7O7, 778.5748; found, 778.5740. Anal. Calcd for C49H78O7: C, 75.54; H, 10.09. Found: C, 75.44; H, 10.20.

Workup

  1. temperatureheated at 150° C. for additional 3 h
  2. customThe reaction mixture was quenched with a saturated NH4Cl aqueous solution
  3. extractionextracted with CH2Cl2
  4. washThe organic phase was washed with H2O
  5. dry with materialdried over anhydrous MgSO4
  6. customThe solvent was removed under reduced pressure
  7. customto give brown oil
  8. customThe crude product was purified by column chromatography (silica gel, hexanes:ethyl acetate=6:1 (v/v))

Sources & evidence

ORD record
ord-4ab7ebe9c27b4a7b8da496ec03abc4e7
Source dataset
uspto-grants-2010_11
Patent number
US07842830B2

Reaction notes

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