Ethyl Acetate → HCID 178510470, compound

HRID 1873595Notes

Reaction equation

HRID 1873595 reaction equation
[NH2:1][C:2]1[C:7]([C:8]#[N:9])=[C:6]([CH:10]2[CH2:15][CH2:14][CH:13]([O:16][CH2:17][CH2:18][O:19][Si](C(C)(C)C)(C3C=CC=CC=3)C3C=CC=CC=3)[CH2:12][CH2:11]2)[C:5]([C:37]#[N:38])=[C:4]([S:39][CH2:40][C:41]2[N:42]=[C:43]([C:46]3[CH:51]=[CH:50][C:49]([Cl:52])=[CH:48][CH:47]=3)[S:44][CH:45]=2)[N:3]=1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.C(OCC)(=O)C>C1COCC1>[NH2:1][C:2]1[C:7]([C:8]#[N:9])=[C:6]([C@H:10]2[CH2:15][CH2:14][C@H:13]([O:16][CH2:17][CH2:18][OH:19])[CH2:12][CH2:11]2)[C:5]([C:37]#[N:38])=[C:4]([S:39][CH2:40][C:41]2[N:42]=[C:43]([C:46]3[CH:47]=[CH:48][C:49]([Cl:52])=[CH:50][CH:51]=3)[S:44][CH:45]=2)[N:3]=1

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 2724141Tetrabutylammonium FluorideHCID 68699977HCID 68699977, compound

Product 1

HCID 178510470HCID 178510470, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

35 mg (0.05 mmol) of the compound from Example 7A (trans isomer) are dissolved in 5 ml of dry THF, 18 mg (0.07 mmol) of tetra-n-butylammonium fluoride are added and the mixture is stirred at RT for 20 h. 15 ml of ethyl acetate are then added to the mixture. The mixture is washed twice with in each case 3 ml of saturated aqueous sodium bicarbonate solution. The organic phase is dried over magnesium sulfate. After removal of the solvent on a rotary evaporator the crude product is purified by preparative HPLC (column: YMC GEL ODS-AQ S-5/15 μm; mobile phase gradient: acetonitrile/water 10:90→95:5).

Workup

  1. washThe mixture is washed twice with in each case 3 ml of saturated aqueous sodium bicarbonate solution
  2. dry with materialThe organic phase is dried over magnesium sulfate
  3. customAfter removal of the solvent
  4. customon a rotary evaporator the crude product
  5. customis purified by preparative HPLC (column: YMC GEL ODS-AQ S-5/15 μm; mobile phase gradient: acetonitrile/water 10:90→95:5)

Sources & evidence

ORD record
ord-d1ecbfceca0f443c92474e9e3e428962
Source dataset
uspto-grants-2012_11
Patent number
US08304412B2

Reaction notes

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