Acetic Acid → HCID 58147578, compound

HRID 1944119Notes

Reaction equation

HRID 1944119 reaction equation
C(O)(=O)C.[C:5]([N:9]([CH3:35])[C:10]([C:12]1[N:16]2[CH2:17][CH2:18][C:19]3[C:24]([C:15]2=[C:14]([C:30]2[S:31][CH:32]=[CH:33][CH:34]=2)[CH:13]=1)=[CH:23][C:22]([N+:25]([O-])=O)=[C:21]([O:28][CH3:29])[CH:20]=3)=[O:11])([CH3:8])([CH3:7])[CH3:6]>C1COCC1.[Zn]>[C:5]([N:9]([CH3:35])[C:10]([C:12]1[N:16]2[CH2:17][CH2:18][C:19]3[C:24]([C:15]2=[C:14]([C:30]2[S:31][CH:32]=[CH:33][CH:34]=2)[CH:13]=1)=[CH:23][C:22]([NH2:25])=[C:21]([O:28][CH3:29])[CH:20]=3)=[O:11])([CH3:7])([CH3:8])[CH3:6]

Participants

5

Reactant 2

HCID 176Acetic AcidHCID 44180405HCID 44180405, compound

Product 1

HCID 58147578HCID 58147578, compound

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 8028TetrahydrofuranSolvent

Procedure

Acetic acid (0.39 ml) was added portionwise to a solution of the product of example 94 (300 mg) in THF (10 ml) at 0° C., followed by the portionwise addition of zinc (893 mg). After stirring for 2 h at room temperature, the reaction mixture was filtered over decalite. The filtrate was concentrated in vacuo and dissolved in ethyl acetate. The organic layer was washed with saturated NaHCO3 solution and brine. The organic layer was dried (MgSO4), filtered and concentrated in vacuo. Residue was purified by preparative HPLC (0→100% acetonitrile; system 1).

Workup

  1. filtrationthe reaction mixture was filtered over decalite
  2. concentrationThe filtrate was concentrated in vacuo
  3. dissolutiondissolved in ethyl acetate
  4. washThe organic layer was washed with saturated NaHCO3 solution and brine
  5. dry with materialThe organic layer was dried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customResidue was purified by preparative HPLC (0→100% acetonitrile; system 1)

Sources & evidence

ORD record
ord-60babd8cbfe047d79dce4988e7e054a9
Source dataset
uspto-grants-2013_03
Patent number
US08394789B2

Reaction notes

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