HCID 69622564, compound → HCID 14110361, compound

HRID 1826128Notes

Reaction equation

HRID 1826128 reaction equation
ClC(Cl)(Cl)COC([N:7]1[C:13]2[CH:14]=[CH:15][C:16]([O:18][CH3:19])=[CH:17][C:12]=2[C:11](=[O:20])[N:10]2[CH2:21][CH2:22][CH2:23][C@H:9]2[C@@H:8]1O)=O>C1COCC1.CCOC(C)=O>[CH3:19][O:18][C:16]1[CH:15]=[CH:14][C:13]2[N:7]=[CH:8][CH:9]3[CH2:23][CH2:22][CH2:21][N:10]3[C:11](=[O:20])[C:12]=2[CH:17]=1

Participants

4

Reactant 1

HCID 69622564HCID 69622564, compound

Product 1

HCID 14110361HCID 14110361, compoundYield 90%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

10% Cd/Pb couple (2.50 g, 20 mmol Cd) was added to a rapidly stirring solution of 95 (1.71 g, 4.03 mmol) in a mixture of THF (30 mL) and 1N NH4OAc (30 mL). Upon addition, the solution turned cloudy and after 2 hours TLC showed the reaction to be complete. The reaction mixture was diluted with EtOAc (150 mL) and dried over anhydrous MgSO4. The solids were filtered and rinsed with EtOAc (50 mL). Removal of excess solvent by rotary evaporation under reduced pressure afforded the product as a yellow solid (0.84 g, 3.6 mmol, 90%).

Workup

  1. additionUpon addition
  2. customthe reaction
  3. dry with materialdried over anhydrous MgSO4
  4. filtrationThe solids were filtered
  5. washrinsed with EtOAc (50 mL)
  6. customRemoval of excess solvent
  7. customby rotary evaporation under reduced pressure

Sources & evidence

ORD record
ord-5df9be46ba67463c88d282146be37afa
Source dataset
uspto-grants-2006_05
Patent number
US07049311B1

Reaction notes

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