Hydrogen Peroxide → HCID 66997518, compound

HRID 1817330Notes

Reaction equation

HRID 1817330 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:23]=[CH:24][C:25]=1[F:26])[CH2:5][N:6]1[CH2:15][CH2:14][C:13]2[C:12]([C:16]([O:18][CH2:19][CH3:20])=[O:17])=[N:11][CH:10]=[C:9]([OH:21])[C:8]=2[C:7]1=[O:22].OO.[O-:29]S([O-])=O.[Na+].[Na+]>C(O)(=O)C>[Cl:1][C:2]1[CH:3]=[C:4]([CH:23]=[CH:24][C:25]=1[F:26])[CH2:5][N:6]1[CH2:15][CH2:14][C:13]2[C:8](=[C:9]([OH:21])[CH:10]=[N+:11]([O-:29])[C:12]=2[C:16]([O:18][CH2:19][CH3:20])=[O:17])[C:7]1=[O:22]

Participants

5

Reactant 3

HCID 784Hydrogen PeroxideHCID 24437Sodium SulfiteHCID 59455599Ethyl 6-(3-chloro-4-fluorobenzyl)-4-hydroxy-5-oxo-5,6,7,8-tetrahydro-2,6-naphthyridine-1-carboxylate

Product 1

HCID 66997518HCID 66997518, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
100 °C

Procedure

Ethyl 6-(3-chloro-4-fluorobenzyl)-4-hydroxy-5-oxo-5,6,7,8-tetrahydro-2,6-naphthyridine-1-carboxylate (22 g, 58 mmol) was dissolved in 500 mL glacial acetic acid and H2O2 (30% by weight in water, 65.8 mL) was added. The reaction was warmed to 100° C. and aged for four hours at which time LCMS showed the reaction done. The solution was cooled in an ice bath to 25° C. and treated with saturated Na2SO3 solution, keeping the temperature below 40° C. When starch paper test showed no peroxides present, the solution was concentrated by ⅓, the pH was adjusted to ˜3 with aqueous HCl and the solution extracted with CH2Cl2 several times. The organic layers were dried over Na2SO4, filtered and evaporated to give product as an oil.

Workup

  1. temperatureThe solution was cooled in an ice bath to 25° C.
  2. customthe temperature below 40° C
  3. concentrationthe solution was concentrated by ⅓
  4. extractionthe solution extracted with CH2Cl2 several times
  5. dry with materialThe organic layers were dried over Na2SO4
  6. filtrationfiltered
  7. customevaporated
  8. customto give product as an oil

Sources & evidence

ORD record
ord-ab3abd6456f84f15bff0f53756496f88
Source dataset
uspto-grants-2009_10
Patent number
US07598264B2

Reaction notes

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