Tetrahydrofuran → HCID 9969252, compound

HRID 1791503Notes

Reaction equation

HRID 1791503 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:8]2[CH:9]=[C:10]3[C:14](=[CH:15][CH:16]=2)[N:13]([CH:17]2[CH2:21][CH2:20][CH2:19][CH2:18]2)[CH:12]=[CH:11]3)[CH:5]=[CH:6][CH:7]=1.[C:22](Cl)([C:24](Cl)=[O:25])=[O:23].C1C[O:31]CC1>>[Cl:1][C:2]1[CH:3]=[C:4]([C:8]2[CH:9]=[C:10]3[C:14](=[CH:15][CH:16]=2)[N:13]([CH:17]2[CH2:21][CH2:20][CH2:19][CH2:18]2)[CH:12]=[C:11]3[C:24](=[O:25])[C:22]([OH:31])=[O:23])[CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 3

HCID 8028TetrahydrofuranHCID 65578Oxalyl chlorideHCID 22032982HCID 22032982, compound

Product 1

HCID 9969252HCID 9969252, compound

Procedure

The product from Step 3 of Example 45 was dissolved in 0.5 ml anhydrous THF and 50 μL (COCl)2 was added. The solution was mixed at room temperature overnight with orbital shaking. An aliquot removed for LC analysis indicated that the reaction was complete. The solution was added to 1 mL aqueous NaHCO3 and the vial was capped and shaken. 0.1 mL 2N HCl was added and the vial was again capped and shaken. The reaction was concentrated to dryness under vacuum. The residue was purified by RP-HPLC (see Note 1 below) to give 6.4 mg of the title compound as an oil.

Workup

  1. additionThe solution was mixed at room temperature overnight with orbital shaking
  2. customAn aliquot removed for LC analysis
  3. additionThe solution was added to 1 mL aqueous NaHCO3
  4. customthe vial was capped
  5. addition0.1 mL 2N HCl was added
  6. customthe vial was again capped
  7. stirringshaken
  8. concentrationThe reaction was concentrated to dryness under vacuum
  9. customThe residue was purified by RP-HPLC (see Note 1 below)

Sources & evidence

ORD record
ord-611af92e7dae4267bc90a76f838d59bc
Source dataset
uspto-grants-2006_07
Patent number
US07074817B2

Reaction notes

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