Hydrochloric Acid → HCID 54739191, compound

HRID 1822423Notes

Reaction equation

HRID 1822423 reaction equation
C(O[C:4](=[O:26])[C:5](=[N:10][N:11]([CH:20]1[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]1)[C:12](=[O:19])[CH2:13][C:14]([O:16]CC)=O)[C:6]([CH3:9])([CH3:8])[CH3:7])C.C1CCN2C(=[N:31]CCC2)CC1.C(C(C(Cl)=O)C(Cl)=O)C.Cl.CC[O:50][C:51]([CH3:53])=[O:52]>O1CCCC1.O>[CH:20]1([N:11]2[C:12](=[O:19])[C:13]([C:14]([NH:31][CH2:53][C:51]([OH:50])=[O:52])=[O:16])=[C:4]([OH:26])[C:5]([C:6]([CH3:9])([CH3:8])[CH3:7])=[N:10]2)[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25]1

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 8857Ethyl AcetateHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 109209242-Ethylpropanedioyl dichlorideHCID 86623018HCID 86623018, compound

Product 1

HCID 54739191HCID 54739191, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Ethyl-2-{cyclohexyl[3-(ethyloxy)-3-oxopropanoyl]hydrazono}-3,3-dimethylbutanoate. DBU (0.21 ml, 1.393 mmol) was added to a solution of the compound from example 99a) (0.323 g, 1.270 mmol) in Tetrahydrofuran (THF) (1 ml) at 0° C. The reaction was brought to room temperature and stirred for 10 minutes. The temperature was then reduced to 0° C. and ethyl malonyl chloride (0.19 ml, 1.410 mmol) was added. The reaction stirred for 2.5 h at room temperature followed by the addition of 1N HCl. The solution was diluted with H2O and EtOAc and the layers separated. The aqueous phase was backextracted with EtOAc several times. The combined organic layers were washed with Brine, dried (MgSO4), filtered and concentrated. The product was purified by column chromatography (SiO2, 5-25% EtOAc/Hexanes) to give a mixture of the title compound and the cyclized product 56c) (197 mg, 42%). LCMS (ES+) m/z 369.0, 323.0 (MH+).

Workup

  1. customwas brought to room temperature
  2. customwas then reduced to 0° C.
  3. stirringThe reaction stirred for 2.5 h at room temperature
  4. customthe layers separated
  5. washThe combined organic layers were washed with Brine
  6. dry with materialdried (MgSO4)
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe product was purified by column chromatography (SiO2, 5-25% EtOAc/Hexanes)
  10. customto give

Sources & evidence

ORD record
ord-59bbbf84161447cdaf7cdb16022f84e1
Source dataset
uspto-grants-2009_10
Patent number
US07608621B2

Reaction notes

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