Oxalic Acid → HCID 20081800, compound

HRID 1609552Notes

Reaction equation

HRID 1609552 reaction equation
[H-].[Na+].[CH3:3][C:4]1[C:9]([CH:10]=O)=[C:8]([C:12]2[CH:17]=[CH:16][C:15]([F:18])=[CH:14][CH:13]=2)[CH:7]=[C:6]([CH3:19])[N:5]=1.[C:20](O)(=O)[C:21](O)=[O:22].[OH-].[Na+]>O1CCCC1.C(#N)C.O.CN(C)C=O>[CH3:3][C:4]1[C:9](/[CH:10]=[CH:20]/[CH:21]=[O:22])=[C:8]([C:12]2[CH:17]=[CH:16][C:15]([F:18])=[CH:14][CH:13]=2)[CH:7]=[C:6]([CH3:19])[N:5]=1

Participants

9

Reactant 4

HCID 971Oxalic AcidHCID 14798Sodium HydroxideHCID 24758Sodium hydrideHCID 9899408HCID 9899408, compound

Product 1

HCID 20081800HCID 20081800, compound

Reagents, catalysts & solvents 4

HCID 962WaterSolvent2×HCID 6228DimethylformamideSolventHCID 6342AcetonitrileSolventHCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

778 mg (3.2 mmol) of diethyl [2-(cyclohexylamino)vinyl]-phosphate in 3 ml of tetrahydrofuran are added under a nitrogen atmosphere to 75.5 mg (3.2 mmol) of sodium hydride in 3 ml of absolute tetrahydrofuran during the course of 15 minutes at 0° C., the mixture is stirred for 15 minutes at 0° C. and a solution of 0.6 g (2.6 mmol) of the compound from Example 30 in 3 ml of acetonitrile/3 ml of dimethylformamide is added dropwise. After stirring for 1 h at 0° C. and 30 minutes at 25° C., the mixture is hydrolyzed using 50 ml of water, washed with ether (3×50 ml), and the organic phase is dried, concentrated in vacuo, taken up in 8 ml of toluene and stirred with 1.2 g (13.5 mmol) of oxalic acid/20 ml of water for 1.5 h at 60° C.-80° C. under a nitrogen atmosphere. After cooling, the mixture is adjusted to pH 10 using 2N sodium hydroxide solution and washed four times with ether, and the ether phase is dried, concentrated in vacuo and chromatographed over 100 g of silica gel using dichloromethane/methanol 30:1.

Workup

  1. stirringAfter stirring for 1 h at 0° C. and 30 minutes at 25° C.
  2. washwashed with ether (3×50 ml)
  3. customthe organic phase is dried
  4. concentrationconcentrated in vacuo
  5. temperatureAfter cooling
  6. washwashed four times with ether
  7. dry with materialthe ether phase is dried
  8. concentrationconcentrated in vacuo
  9. customchromatographed over 100 g of silica gel

Sources & evidence

ORD record
ord-c8457d8cfe4240e199ffa5181c8e8f82
Source dataset
uspto-grants-1995_03
Patent number
US05401746

Reaction notes

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