Water → HCID 87220312, compound

HRID 1436975Notes

Reaction equation

HRID 1436975 reaction equation
[H-].[Na+].[CH2:3]([O:5][CH:6]([O:8][CH:9]1[CH2:21][CH2:20][C:19]([O:23][CH:24]([O:26][CH2:27][CH3:28])[CH3:25])([CH3:22])[CH:18]([OH:29])[CH:17]=[CH:16][CH:15]([CH3:30])[CH:14](/[C:31](/[CH3:58])=[CH:32]/[CH:33]=[CH:34]/[C:35]([O:52][CH:53]([O:55][CH2:56][CH3:57])[CH3:54])([CH3:51])[CH2:36][CH:37]2[O:50][CH:38]2[CH:39]([CH3:49])[CH:40]([O:43][CH:44]([O:46][CH2:47][CH3:48])[CH3:45])[CH2:41][CH3:42])[O:13][C:11](=[O:12])[CH2:10]1)[CH3:7])[CH3:4].[CH:59]([N:62]=[C:63]=[S:64])([CH3:61])[CH3:60].O>O1CCCC1.C(OCC)(=O)C>[CH2:3]([O:5][CH:6]([O:8][CH:9]1[CH2:21][CH2:20][C:19]([O:23][CH:24]([O:26][CH2:27][CH3:28])[CH3:25])([CH3:22])[CH:18]([O:29][C:63](=[S:64])[NH:62][CH:59]([CH3:61])[CH3:60])[CH:17]=[CH:16][CH:15]([CH3:30])[CH:14](/[C:31](/[CH3:58])=[CH:32]/[CH:33]=[CH:34]/[C:35]([O:52][CH:53]([O:55][CH2:56][CH3:57])[CH3:54])([CH3:51])[CH2:36][CH:37]2[O:50][CH:38]2[CH:39]([CH3:49])[CH:40]([O:43][CH:44]([O:46][CH2:47][CH3:48])[CH3:45])[CH2:41][CH3:42])[O:13][C:11](=[O:12])[CH2:10]1)[CH3:7])[CH3:4]

Participants

7

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 75263Isopropyl IsothiocyanateHCID 86602606HCID 86602606, compound

Product 1

HCID 87220312HCID 87220312, compoundYield 60%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

To a suspension of sodium hydride (60% oil dispersion, 2 mg, 0.052 mmol) in tetrahydrofuran (0.5 mL) was added dropwise a solution of (8E,12E,14E)-3,6,16,21-tetra(1-ethoxyethoxy)-7-hydroxy-6,10,12,16,20-pentamethyl-18,19-epoxytricosa-8,12,14-trien-11-olide (19 mg, 0.019 mmol) obtained in Example 3-(2) in tetrahydrofuran (0.5 mL) under ice-cooling and stirring, and the reaction mixture was stirred at room temperature for 10 minutes. Then, isopropyl isothiocyanate (6.6 mg, 0.066 mmol) was added dropwise thereto, and the reaction mixture was stirred at room temperature for three hours. Water was added to the reaction mixture under ice-cooling to terminate the reaction, followed by diluting with ethyl acetate and washing with brine. The organic layer was dried over anhydrous sodium sulfate and evaporated. The resulting residue was purified by silica gel column chromatography (Kanto silica gel 60N, 40 to 100 μm; ethyl acetate:hexane=25:75) to give the title compound (10 mg, 60%) as a colorless oil.

Workup

  1. temperaturecooling
  2. stirringthe reaction mixture was stirred at room temperature for 10 minutes
  3. stirringthe reaction mixture was stirred at room temperature for three hours
  4. temperaturecooling
  5. customto terminate
  6. customthe reaction
  7. washwashing with brine
  8. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  9. customevaporated
  10. customThe resulting residue was purified by silica gel column chromatography (Kanto silica gel 60N, 40 to 100 μm; ethyl acetate:hexane=25:75)

Sources & evidence

ORD record
ord-ba6f89771add492aa5f406d3cfc194c2
Source dataset
uspto-grants-2009_11
Patent number
US07619100B2

Reaction notes

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