HCID 23574472, compound → HCID 22046725, compound

HRID 1826136Notes

Reaction equation

HRID 1826136 reaction equation
[CH3:1][O:2][C:3]1[C:4]([O:29][CH3:30])=[C:5]([O:27][CH3:28])[C:6]2[N:12](C(OCC(Cl)(Cl)Cl)=O)[C@@H:11](O)[C@@H:10]3[CH2:22][CH2:23][CH2:24][N:9]3[C:8](=[O:25])[C:7]=2[CH:26]=1>C1COCC1.CCOC(C)=O>[CH3:1][O:2][C:3]1[C:4]([O:29][CH3:30])=[C:5]([O:27][CH3:28])[C:6]2[N:12]=[CH:11][CH:10]3[CH2:22][CH2:23][CH2:24][N:9]3[C:8](=[O:25])[C:7]=2[CH:26]=1

Participants

4

Reactant 1

HCID 23574472HCID 23574472, compound

Product 1

HCID 22046725HCID 22046725, compoundYield 95.2%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

10% Cd/Pb couple (1.25 g, 10 mmol Cd) was added to a rapidly stirring solution of the Troc-carbamate, 119 (1.00 g, 2.1 mmol) in a mixture of THF (13 mL) and 1N NH4OAc (B mL). Upon addition, the reaction mixture went cloudy. After 40 minutes, TLC showed the reaction to be complete and the reaction mixture was diluted with EtOAc (200 mL). The solution was dried over anhydrous MgSO4 and the solids were filtered and rinsed with EtOAc (50 mL). Evaporation of the solvent yielded the product as a yellow glass (0.581 g, 2.0 mmol). 1H NMR (270 MHz, CDCl3) δ 7.73 (d, 1H, J=4.57 Hz), 7.08 (s, 1H), 4.0-3.4 (m, 12H), 2.4-1.8 (m, 4H).

Workup

  1. additionUpon addition
  2. customthe reaction
  3. dry with materialThe solution was dried over anhydrous MgSO4
  4. filtrationthe solids were filtered
  5. washrinsed with EtOAc (50 mL)
  6. customEvaporation of the solvent

Sources & evidence

ORD record
ord-82ace3483183424eae3ee88aa43647c0
Source dataset
uspto-grants-2006_05
Patent number
US07049311B1

Reaction notes

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