Potassium Bromide → HCID 23077665, compound

HRID 1349461Notes

Reaction equation

HRID 1349461 reaction equation
[CH2:1]([O:8][C:9]1[C:10](=[O:31])[CH:11]=[C:12]([CH2:29][OH:30])[N:13]2[CH2:18][CH2:17][N:16]([CH2:19][C:20]3[CH:25]=[CH:24][C:23]([Cl:26])=[C:22]([Cl:27])[CH:21]=3)[C:15](=[O:28])[C:14]=12)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(=O)([O-])[OH:33].[Na+].[Br-].[K+].CC1(C)N([O])C(C)(C)CCC1.Cl[O-].[Na+].S([O-])(O)(=O)=O.[K+]>CC(C)=O>[CH2:1]([O:8][C:9]1[C:10](=[O:31])[CH:11]=[C:12]([C:29]([OH:33])=[O:30])[N:13]2[CH2:18][CH2:17][N:16]([CH2:19][C:20]3[CH:25]=[CH:24][C:23]([Cl:26])=[C:22]([Cl:27])[CH:21]=3)[C:15](=[O:28])[C:14]=12)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

8

Reactant 6

HCID 253877Potassium BromideHCID 516892Sodium BicarbonateHCID 516920Potassium bisulfateHCID 2724126TempoHCID 23077651HCID 23077651, compoundHCID 23665760Sodium Hypochlorite

Product 1

HCID 23077665HCID 23077665, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

9-Benzyloxy-2-(3,4-dichlorobenzyl)-6-hydroxymethyl-3,4-dihydro-2H-pyrido[1,2-a]pyrazine-1,8-dione (100 mg) obtained in Example 5, Step 6 was dissolved in acetone (1.6 ml) and saturated aqueous sodium hydrogen carbonate solution (1.0 ml) and potassium bromide (3 mg), 2,2,6,6-tetramethylpiperidine 1-oxyl and free radical (3 mg) were added, and 6% aqueous sodium hypochlorite solution (3.4 ml) was added dropwise under ice-cooling. After stirring for 15 min, the ice bath was removed and the mixture was stirred at room temperature for 4 hr. Furthermore, 6% aqueous sodium hypochlorite solution (0.1 ml) was added dropwise and the mixture was stirred for 1.5 hr. The obtained reaction mixture was poured into 5% aqueous potassium hydrogen sulfate solution and stirred for 30 min. The resulting crystals were collected by filtration to give 9-benzyloxy-2-(3,4-dichlorobenzyl)-1,8-dioxo-1,3,4,8-tetrahydro-2H-pyrido[1,2-a]pyrazine-6-carboxylic acid (94 mg).

Workup

  1. temperaturecooling
  2. customthe ice bath was removed
  3. stirringthe mixture was stirred at room temperature for 4 hr
  4. additionFurthermore, 6% aqueous sodium hypochlorite solution (0.1 ml) was added dropwise
  5. stirringthe mixture was stirred for 1.5 hr
  6. customThe obtained reaction mixture
  7. stirringstirred for 30 min
  8. filtrationThe resulting crystals were collected by filtration

Sources & evidence

ORD record
ord-069466b25d504bb1ba0e538a1c149a10
Source dataset
uspto-grants-2007_05
Patent number
US07211572B2

Reaction notes

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