Peracetic Acid → HCID 69058844, compound

HRID 1817337Notes

Reaction equation

HRID 1817337 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]([N:18]([CH3:20])[CH3:19])=[O:17])=[N:11][CH:10]=[C:9]([OH:21])[C:8]=2[C:7]1=[O:22].C(OO)(=[O:29])C.C([O-])(=O)C.[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]([N:18]([CH3:19])[CH3:20])=[O:17])[C:7]1=[O:22]

Participants

5

Reactant 3

HCID 6585Peracetic AcidHCID 517045Sodium AcetateHCID 69059310HCID 69059310, compound

Product 1

HCID 69058844HCID 69058844, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
50 °C

Procedure

6-(3-Chloro-4-fluorobenzyl)-4-hydroxy-N,N-dimethyl-5-oxo-5,6,7,8-tetrahydro-2,6-naphthyridine-1-carboxamide (24 g, 63.5 mmol) was dissolved in 1000 mL glacial acetic acid and per-acetic acid (32% by weight in acetic acid, 151 mL, 635 mmol) and sodium acetate (2.6 g, 31.7 mmol) was added. The reaction was warmed to 50° C. and aged overnight at which time LCMS showed the reaction done. The solution reduced in volume to ⅓ on the rotoevaporator, cooled in an ice bath and quenched slowly with 10% Na2SO3 solution until no peroxide was detected by a starch paper test. The reaction was transferred to a separatory funnel and water (500 mL) and chloroform was added. The layers were separated and the water extracted with CHCl3 several times. The combined organic layers were washed with slightly acidic water, brine and dried over Na2SO4, filtered and evaporated to give the product as an oil. The initial NMR shows an excessive number of methyl group peaks, perhaps as a result of oxalyl chloride reacting with dimethylamine in the second step and this impurity being carried through. A small sample was purified by reverse phase chromatography eluting with 95:5-5:95 water/acetonitrile 0.1% TFA to give clean material for NMR.

Workup

  1. temperaturecooled in an ice bath
  2. customquenched slowly with 10% Na2SO3 solution until no peroxide
  3. customThe reaction was transferred to a separatory funnel
  4. additionwater (500 mL) and chloroform was added
  5. customThe layers were separated
  6. extractionthe water extracted with CHCl3 several times
  7. washThe combined organic layers were washed with slightly acidic water, brine
  8. dry with materialdried over Na2SO4
  9. filtrationfiltered
  10. customevaporated

Sources & evidence

ORD record
ord-a788115076f14c6ba04106659284e9bc
Source dataset
uspto-grants-2009_10
Patent number
US07598264B2

Reaction notes

Loading…