Ethyl Acetate → HCID 117831128, compound

HRID 518934Notes

Reaction equation

HRID 518934 reaction equation
[F-].C([N+](CCCC)(CCCC)CCCC)CCC.[Si]([O:26][C:27]1[CH:32]=[CH:31][C:30]([N:33]([C:80]2[CH:81]=[C:82]3[CH:88]=[CH:87][N:86]([CH3:89])[C:83]3=[N:84][CH:85]=2)[C:34]([C:36]2[CH:37]=[C:38]([C:45]3[CH:50]=[CH:49][C:48]([O:51][CH2:52][C:53](=[O:60])[N:54]4[CH2:59][CH2:58][CH2:57][CH2:56][CH2:55]4)=[CH:47][C:46]=3[C:61]([N:63]3[C@H:72]([CH2:73][N:74]4[CH2:79][CH2:78][O:77][CH2:76][CH2:75]4)[CH2:71][C:70]4[C:65](=[CH:66][CH:67]=[CH:68][CH:69]=4)[CH2:64]3)=[O:62])[N:39]3[C:44]=2[CH2:43][CH2:42][CH2:41][CH2:40]3)=[O:35])=[CH:29][CH:28]=1)(C(C)(C)C)(C)C.C(OCC)(=O)C.C([O-])(O)=O.[Na+]>O1CCCC1>[OH:26][C:27]1[CH:28]=[CH:29][C:30]([N:33]([C:80]2[CH:81]=[C:82]3[CH:88]=[CH:87][N:86]([CH3:89])[C:83]3=[N:84][CH:85]=2)[C:34]([C:36]2[CH:37]=[C:38]([C:45]3[CH:50]=[CH:49][C:48]([O:51][CH2:52][C:53](=[O:60])[N:54]4[CH2:59][CH2:58][CH2:57][CH2:56][CH2:55]4)=[CH:47][C:46]=3[C:61]([N:63]3[C@H:72]([CH2:73][N:74]4[CH2:75][CH2:76][O:77][CH2:78][CH2:79]4)[CH2:71][C:70]4[C:65](=[CH:66][CH:67]=[CH:68][CH:69]=4)[CH2:64]3)=[O:62])[N:39]3[C:44]=2[CH2:43][CH2:42][CH2:41][CH2:40]3)=[O:35])=[CH:31][CH:32]=1

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 516892Sodium BicarbonateHCID 2724141Tetrabutylammonium FluorideHCID 131733365HCID 131733365, compound

Product 1

HCID 117831128HCID 117831128, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A 1M solution of tetrabutylammonium fluoride (3.14 mL, 3 mmol) in tetrahydrofuran is added at ambient temperature to a solution, in 30 mL of tetrahydrofuran, of the compound obtained in Step E (2.92 g, 2.9 mmol). After stirring for 5 minutes, the reaction mixture is poured into a 50/50 mixture of ethyl acetate and saturated aqueous NaHCO3 solution. The separated organic phase is washed with water and then with brine. The combined aqueous phases are extracted with ethyl acetate. The resulting organic phases are dried over sodium sulphate, filtered and concentrated under reduced pressure. The crude product obtained is purified by chromatography over silica gel (dichloromethane/ethanol/ammonia gradient) to yield the title compound.

Workup

  1. washThe separated organic phase is washed with water
  2. extractionThe combined aqueous phases are extracted with ethyl acetate
  3. dry with materialThe resulting organic phases are dried over sodium sulphate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe crude product obtained
  7. customis purified by chromatography over silica gel (dichloromethane/ethanol/ammonia gradient)

Sources & evidence

ORD record
ord-70cec5eade95464b848c23b48f10f806
Source dataset
uspto-grants-2015_08
Patent number
US09115159B2

Reaction notes

Loading…