Ethyl Acetate → HCID 19426979, compound

HRID 260449Notes

Reaction equation

HRID 260449 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:26]([OH:42])([C:29]2[N:30](COCC[Si](C)(C)C)[CH:31]=[CH:32][N:33]=2)[CH2:27][CH3:28])[CH:5]=[C:6]([CH:25]=1)[O:7][CH2:8][C:9]1[CH:18]=[C:17]2[C:12]([C:13]([C:20]3[CH:24]=[CH:23][O:22][CH:21]=3)=[CH:14][C:15](=[O:19])[O:16]2)=[CH:11][CH:10]=1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.C(OCC)(=O)C>C1COCC1>[F:1][C:2]1[CH:3]=[C:4]([C:26]([OH:42])([C:29]2[NH:33][CH:32]=[CH:31][N:30]=2)[CH2:27][CH3:28])[CH:5]=[C:6]([CH:25]=1)[O:7][CH2:8][C:9]1[CH:18]=[C:17]2[C:12]([C:13]([C:20]3[CH:24]=[CH:23][O:22][CH:21]=3)=[CH:14][C:15](=[O:19])[O:16]2)=[CH:11][CH:10]=1

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 2724141Tetrabutylammonium FluorideHCID 19426931HCID 19426931, compound

Product 1

HCID 19426979HCID 19426979, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
55 °C

Procedure

Under N2 the compound from Step 1 (94 mg, 0.159 mmol) was dissolved in THF (2 mL). Tetrabutylammonium fluoride was added (795 μL, 0.795 mmol) and the reaction was stirred at 55° C. for 1 h. Ethyl acetate was added and the organic phase was washed with brine, dried over MgSO4, filtered and evaporated to give an oil which was purified by a flash silica column using EtOAc then 5% MeOH in CH2Cl2 as the eluent. The title compound was obtained: 12.8 mg (17%). Mass spec.: 461 (MH+).

Workup

  1. washthe organic phase was washed with brine
  2. dry with materialdried over MgSO4
  3. filtrationfiltered
  4. customevaporated
  5. customto give an oil which
  6. customwas purified by a flash silica column

Sources & evidence

ORD record
ord-07af672d548c482db8a05a018e92ab93
Source dataset
uspto-grants-1996_06
Patent number
US05527827

Reaction notes

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