Tetrahydrofuran → HCID 25181716, compound

HRID 1697068Notes

Reaction equation

HRID 1697068 reaction equation
[CH3:1][O:2][C:3]([C:5]1[N:6]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[C:7]2[C:12]([C:13](=[O:26])[C:14]=1[CH2:15][C:16]1[CH:21]=[CH:20][C:19](SCCO)=[CH:18][CH:17]=1)=[CH:11][CH:10]=[C:9]([Cl:27])[CH:8]=2)=[O:4].O[O:35][S:36]([O-:38])=O.[K+].C([O-])(O)=O.[Na+].C1C[O:48][CH2:47][CH2:46]1>CO.O>[CH3:1][O:2][C:3]([C:5]1[N:6]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[C:7]2[C:12]([C:13](=[O:26])[C:14]=1[CH2:15][C:16]1[CH:21]=[CH:20][C:19]([S:36]([CH2:46][CH2:47][OH:48])(=[O:38])=[O:35])=[CH:18][CH:17]=1)=[CH:11][CH:10]=[C:9]([Cl:27])[CH:8]=2)=[O:4]

Participants

7

Reactant 4

HCID 8028TetrahydrofuranHCID 516892Sodium BicarbonateHCID 23707502Potassium hydroxy sulfiteHCID 59846161HCID 59846161, compound

Product 1

HCID 25181716HCID 25181716, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To 7-chloro-3-[4-(2-hydroxy-ethylsulfanyl)-benzyl]-4-oxo-1-phenyl-1,4-dihydro-quinoline-2-carboxylic acid methyl ester (100 mg) in a mixture of THF and MeOH (1:5, 12 mL) was added a solution of OXONE™ (294 mg) in water (3 mL) at 0° C. The reaction mixture was stirred for 1.5 h, and NaHCO3 (sat aq, 20 mL) added. The resulting mixture was extracted with EtOAc (3×25 mL). The combined organic extracts were washed with brine, dried over Na2SO4, filtered and evaporated under reduced pressure to give a yellow-brown oil. The crude residue was purified by flash chromatography (EtOAc/hexane) to give 7-chloro-3-[4-(2-hydroxyethane-sulfonyl)-benzyl]-4-oxo-1-phenyl-1,4-dihydro-quinoline-2-carboxylic acid methyl ester (23.6 mg) as an off-white powder. MS=512 [M+H]+; MP=172.2-173.5° C.

Workup

  1. extractionThe resulting mixture was extracted with EtOAc (3×25 mL)
  2. washThe combined organic extracts were washed with brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. customevaporated under reduced pressure
  6. customto give a yellow-brown oil
  7. customThe crude residue was purified by flash chromatography (EtOAc/hexane)

Sources & evidence

ORD record
ord-053b3e148d33452ab9b80eb76bab2bf3
Source dataset
uspto-grants-2012_04
Patent number
US08163906B2

Reaction notes

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