3-Furaldehyde → HCID 21097179, compound

HRID 1350717Notes

Reaction equation

HRID 1350717 reaction equation
[O:1]1[CH:5]=[CH:4][C:3]([CH:6]=O)=[CH:2]1.[C:8]([O-])([O-])=O.[K+].[K+].[N:14]([C:17]1[CH:18]=[C:19]([CH:40]=[CH:41][C:42]=1[CH3:43])[C:20]([NH:22][C:23]1[CH:28]=[C:27]([C:29]([CH3:32])([CH3:31])[CH3:30])[CH:26]=[C:25]([NH:33][S:34]([CH3:37])(=[O:36])=[O:35])[C:24]=1[O:38][CH3:39])=[O:21])=[N+:15]=[N-:16].O=C1O[C@H]([C@H](CO)O)C([O-])=C1O.[Na+]>CO.O.[O-]S([O-])(=O)=O.[Cu+2]>[C:29]([C:27]1[CH:26]=[C:25]([NH:33][S:34]([CH3:37])(=[O:35])=[O:36])[C:24]([O:38][CH3:39])=[C:23]([NH:22][C:20](=[O:21])[C:19]2[CH:40]=[CH:41][C:42]([CH3:43])=[C:17]([N:14]3[CH:8]=[C:6]([C:3]4[CH:4]=[CH:5][O:1][CH:2]=4)[N:16]=[N:15]3)[CH:18]=2)[CH:28]=1)([CH3:31])([CH3:32])[CH3:30]

Participants

8

Reactant 4

HCID 103513-FuraldehydeHCID 11430Potassium CarbonateHCID 210792023-azido-N-(5-tert-butyl-3-methanesulfonylamino-2-methoxy-phenyl)-4-methyl-benzamideHCID 23667548Sodium Ascorbate

Product 1

HCID 21097179HCID 21097179, compound

Reagents, catalysts & solvents 3

HCID 24462Copper SulfateCatalystHCID 887MethanolSolvent2×HCID 962WaterSolvent

Procedure

To a solution of 96 mg (0.20 mmol) of furan-3-carbaldehyde (Aldrich) and dimethyl 2-oxo-1-diazopropylphosphinate (46 mg; 0.24 mmol) in 1.5 mL of MeOH was added 55.6 mg (0.402 mmol) of K2CO3. The mixture was stirred for 4 h and 58 mg (0.134 mmol) of 3-azido-N-(5-tert-butyl-3-methanesulfonylamino-2-methoxy-phenyl)-4-methyl-benzamide was then added followed by an additional 1 mL of MeOH and 27 mg of sodium ascorbate in 0.2 mL of water. The mixture was vigorously stirred and 0.13 mL (0.013 mmol) of 0.1 M CuSO4 was added. The head space was purged with N2, and the vessel was sealed for 20 h. The mixture was then partitioned between EtOAc and 1M HCl, and the extract was washed with saturated NaHCO3 and brine. The extract was then dried with Na2SO4, filtered, concentrated, and chromatographed (10–50% EtOAc in hexanes) to provide 57 mg (0.11 mmol; 81%) of Example 39. ES MS m/z 524 [C26H29N5O5S+H]+.

Workup

  1. stirringThe mixture was vigorously stirred
  2. customThe head space was purged with N2
  3. customthe vessel was sealed for 20 h
  4. customThe mixture was then partitioned between EtOAc and 1M HCl
  5. washthe extract was washed with saturated NaHCO3 and brine
  6. dry with materialThe extract was then dried with Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customchromatographed (10–50% EtOAc in hexanes)
  10. customto provide 57 mg (0.11 mmol; 81%) of Example 39

Sources & evidence

ORD record
ord-8f842647ce9a4f4f99599b6ffaf8b2b6
Source dataset
uspto-grants-2007_05
Patent number
US07214802B2

Reaction notes

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