Oxalic Acid → HCID 69743753, compound

HRID 2183861Notes

Reaction equation

HRID 2183861 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:23]#[N:24])=[C:6]([CH:22]=1)[O:7][C@@H:8]([CH2:19][O:20][CH3:21])[CH2:9][CH2:10][NH:11]C(=O)OC(C)(C)C.[C:25]([OH:30])(=[O:29])[C:26]([OH:28])=[O:27]>Cl.O1CCOCC1>[C:25]([OH:30])(=[O:29])[C:26]([OH:28])=[O:27].[NH2:11][CH2:10][CH2:9][C@@H:8]([O:7][C:6]1[CH:22]=[C:2]([Cl:1])[CH:3]=[CH:4][C:5]=1[C:23]#[N:24])[CH2:19][O:20][CH3:21]

Participants

5

Reactant 2

HCID 971Oxalic AcidHCID 90906720HCID 90906720, compound

Product 1

HCID 69743753HCID 69743753, compoundYield 22%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 312751,4-DioxaneSolvent

Procedure

The product from step (e) (140 mg, 0.39 mmol) was dissolved in 4M hydrochloric acid in dioxan and stirred at room temperature for 2 h. The solvent was removed in vacuo and the residue partitioned between ethyl acetate and aqueous saturated sodium bicarbonate solution. The organic layer was separated and washed with water (2×20 ml), dried (magnesium sulphate) and evaporated in vacuo. The residue was dissolved in ethyl acetate (5 ml) and treated with one equivalent of oxalic acid. The precipitated solid was filtered off and dried to give the title compound (30 mg, 22%).

Workup

  1. customThe solvent was removed in vacuo
  2. customthe residue partitioned between ethyl acetate and aqueous saturated sodium bicarbonate solution
  3. customThe organic layer was separated
  4. washwashed with water (2×20 ml)
  5. dry with materialdried (magnesium sulphate)
  6. customevaporated in vacuo
  7. dissolutionThe residue was dissolved in ethyl acetate (5 ml)
  8. filtrationThe precipitated solid was filtered off
  9. customdried

Sources & evidence

ORD record
ord-a07f4ebec0834728bc90d6ae7f596871
Source dataset
uspto-grants-2005_05
Patent number
US06900243B2

Reaction notes

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