HCID 86707877, compound → HCID 68357009, compound

HRID 588993Notes

Reaction equation

HRID 588993 reaction equation
COC1C=CC(C[N:8]2[C:12](=[O:13])[C:11]3([CH2:25][C:16]4=[N:17][CH:18]=[C:19]([C:21]([O:23][CH3:24])=[O:22])[CH:20]=[C:15]4[CH2:14]3)[N:10]([CH3:26])[C:9]2=[O:27])=CC=1>C(#N)C.O>[CH3:26][N:10]1[C:11]2([CH2:25][C:16]3=[N:17][CH:18]=[C:19]([C:21]([O:23][CH3:24])=[O:22])[CH:20]=[C:15]3[CH2:14]2)[C:12](=[O:13])[NH:8][C:9]1=[O:27]

Participants

4

Reactant 1

HCID 86707877HCID 86707877, compound

Product 1

HCID 68357009HCID 68357009, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

To a solution of methyl 1′-(4-methoxybenzyl)-3′-methyl-2′,5′-dioxo-5,7-dihydrospiro[cyclopenta[b]pyridine-6,4′-imidazolidine]-3-carboxylate (100 mg, 0.25 mmol) in acetonitrile (8.4 mL) at ambient temperature was added ceric ammonium nitrate (4.1 g, 7.6 mmol) as a solution in H2O (5 mL). After 20 min, the reaction mixture was partitioned between H2O (50 mL) and 9:1-CH2Cl2:i-PrOH (50 mL). The aqueous was extracted further with 9:1 CH2Cl2:i-PrOH (5×50 mL) and the combined organic extracts were dried over sodium sulfate, filtered, and concentrated in vacuo. The crude solid was washed with MTBE (3×10 mL) then partitioned between saturated aqueous sodium bicarbonate (5 mL) and EtOAc (10 mL). The aqueous layer was extracted further with EtOAc (10 mL) and the combined organic extracts were dried over sodium sulfate, filtered, and concentrated in vacuo to provide the title compound in sufficient purity for use in the next step. MS: m/z=276.1 (M+1).

Workup

  1. customthe reaction mixture was partitioned between H2O (50 mL) and 9
  2. extractionThe aqueous was extracted further with 9:1 CH2Cl2
  3. dry with materiali-PrOH (5×50 mL) and the combined organic extracts were dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. washThe crude solid was washed with MTBE (3×10 mL)
  7. customthen partitioned between saturated aqueous sodium bicarbonate (5 mL) and EtOAc (10 mL)
  8. extractionThe aqueous layer was extracted further with EtOAc (10 mL)
  9. dry with materialthe combined organic extracts were dried over sodium sulfate
  10. filtrationfiltered
  11. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-2d42c57f9f4c4f4ba4696f55c4877a6e
Source dataset
uspto-grants-2016_01
Patent number
US09227973B2

Reaction notes

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