Hydrochloric Acid → HCID 54739192, compound

HRID 2046293Notes

Reaction equation

HRID 2046293 reaction equation
C(O[C:4](=[O:25])[C:5](=[N:9][N:10]([CH:19]1[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]1)[C:11](=[O:18])[CH2:12][C:13]([O:15]CC)=O)[CH:6]([CH3:8])[CH3:7])C.C1CCN2C(=[N:30]CCC2)CC1.C(C(C(Cl)=O)C(Cl)=O)C.Cl.CC[O:49][C:50]([CH3:52])=[O:51]>O1CCCC1.O>[CH:19]1([N:10]2[C:11](=[O:18])[C:12]([C:13]([NH:30][CH2:52][C:50]([OH:49])=[O:51])=[O:15])=[C:4]([OH:25])[C:5]([CH:6]([CH3:7])[CH3:8])=[N:9]2)[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24]1

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 8857Ethyl AcetateHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 109209242-Ethylpropanedioyl dichlorideHCID 86760971HCID 86760971, compound

Product 1

HCID 54739192HCID 54739192, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Ethyl-2-{cyclohexyl[3-(ethyloxy)-3-oxopropanoyl]hydrazono}-3-methylbutanoate. DBU (0.35 ml, 2.322 mmol) was added to a solution of the compound from example 98a) (0.51 g, 2.122 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 (0.32 ml, 2.374 mmol) was added. The reaction was brought to room temperature and stirred for 2.5 h. 1N HCl was added and the solution diluted with H2O and EtOAc. The layers were separated and aqueous phase 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, 10-25% EtOAc/Hexanes) to give a mixture of the title compound and the cyclized product 55c) (126 mg, 13%). LCMS (ES+) m/z 355.2, 309.2 (MH+).

Workup

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

Sources & evidence

ORD record
ord-e60d8d059a5a4393832fe7ce153ad863
Source dataset
uspto-grants-2013_11
Patent number
USRE044613E1

Reaction notes

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