Oxalic Acid → HCID 86589163, compound

HRID 2305016Notes

Reaction equation

HRID 2305016 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([S:9]([CH2:12][C:13]2([C:16]([O:18][CH2:19][CH3:20])=[O:17])[CH2:15][O:14]2)(=[O:11])=[O:10])=[CH:5][CH:4]=1.B(F)(F)F.CC[O:27]CC.[C:30](#[N:37])[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1.C(O)(=O)C(O)=O>C(Cl)Cl>[OH:14][C:13]([CH2:12][S:9]([C:6]1[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=1)(=[O:11])=[O:10])([CH2:15][NH:37][C:30]([C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)=[O:27])[C:16]([O:18][CH2:19][CH3:20])=[O:17]

Participants

6

Reactant 4

HCID 971Oxalic AcidHCID 7505BenzonitrileHCID 8000Boron trifluoride etherate2×HCID 86589160HCID 86589160, compound

Product 1

HCID 86589163HCID 86589163, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
65 °C

Procedure

2-Methoxybenzenesulfonyl)methyl-oxiranecarboxylic acid, ethyl ester (from EXAMPLE 1, Step 2, 0.3 g, 1 mmol), boron trifluoride etherate (0.495 mL, 4.0 mmol), and benzonitrile (0.36 mL, 4.0 mmol) are dissolved in 40 mL of methylene chloride. The reaction mixture is stirred at ambient temperature under a nitrogen atmosphere for three days, with the addition two times of 0.50 mL of boron trifluoride etherate. The solvent is removed under reduced pressure. The residue is dissolved in ethyl acetate and washed with saturated sodium bicarbonate and with brine, and dried over magnesium sulfate. The crude product is dissolved in 40 mL of absolute ethanol. Oxalic acid (0.30 g, 3.3 mmol) is added, and the solution is heated to 65° C. for 19 hours. The solvent is removed under reduced pressure. The oily residue is dissolved in ethyl acetate and washed with saturated sodium bicarbonate and with brine, and dried over magnesium sulfate. Chromatography on silica gel, eluting with 1:1 ethyl acetate:hexanes affords the title compound as a white solid. 1H NMR (CDCl3) δ 7.82-7.71, 7.55-7.41, 7.02-6.99, 6.57, 4.29-4.17, 3.88, 3.85-3.72, 3.60-3.56, 1.32-1.28; MS (ES+) 422.1 (M+H), (ES−) 420.1 (M−H).

Workup

  1. customThe solvent is removed under reduced pressure
  2. dissolutionThe residue is dissolved in ethyl acetate
  3. washwashed with saturated sodium bicarbonate and with brine
  4. dry with materialdried over magnesium sulfate
  5. dissolutionThe crude product is dissolved in 40 mL of absolute ethanol
  6. customThe solvent is removed under reduced pressure
  7. dissolutionThe oily residue is dissolved in ethyl acetate
  8. washwashed with saturated sodium bicarbonate and with brine
  9. dry with materialdried over magnesium sulfate
  10. washChromatography on silica gel, eluting with 1:1 ethyl acetate

Sources & evidence

ORD record
ord-b658742fb40a4d6aaf162b3ac7f0fdec
Source dataset
uspto-grants-2002_08
Patent number
US06437177B1

Reaction notes

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