Tetrabutylammonium Fluoride → HCID 59846203, compound

HRID 1697077Notes

Reaction equation

HRID 1697077 reaction equation
[F-].C([N+](CCCC)(CCCC)CCCC)CCC.[CH3:19][O:20][C:21]([C:23]1[N:24]([C:56]2[CH:61]=[CH:60][CH:59]=[CH:58][CH:57]=2)[C:25]2[C:30]([C:31](=[O:54])[C:32]=1[CH2:33][C:34]1[CH:39]=[CH:38][C:37]([S:40](=[O:53])(=[O:52])[NH:41][CH2:42][CH2:43][O:44][Si](C(C)(C)C)(C)C)=[CH:36][CH:35]=1)=[CH:29][CH:28]=[C:27]([Cl:55])[CH:26]=2)=[O:22]>C1COCC1>[CH3:19][O:20][C:21]([C:23]1[N:24]([C:56]2[CH:61]=[CH:60][CH:59]=[CH:58][CH:57]=2)[C:25]2[C:30]([C:31](=[O:54])[C:32]=1[CH2:33][C:34]1[CH:35]=[CH:36][C:37]([S:40](=[O:52])(=[O:53])[NH:41][CH2:42][CH2:43][OH:44])=[CH:38][CH:39]=1)=[CH:29][CH:28]=[C:27]([Cl:55])[CH:26]=2)=[O:22]

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 25181857HCID 25181857, compound

Product 1

HCID 59846203HCID 59846203, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of tetrabutylammonium fluoride (1 M in THF, 0.26 mL) was added to a solution of 3-{4-[2-(tert-butyl-dimethyl-silanyloxy)-ethylsulfamoyl]-benzyl}-7-chloro-4-oxo-1-phenyl-1,4-dihydroquinoline-2-carboxylic acid methyl ester (113 mg) in THF (5 mL) and the resulting mixture was stirred for 1 h. The reaction mixture was partitioned between EtOAc and water, the organic layer separated and the aqueous layer was extracted with EtOAc (2×25 mL). The combined organic extracts were washed with brine, dried over anhydrous Na2SO4, filtered and evaporated under reduced pressure. The yellow solid residue was purified by flash chromatography (DCM/MeOH, 90/10) to afford 7-chloro-3-[4-(2-hydroxy-ethylsulfamoyl)-benzyl]-4-oxo-1-phenyl-1,4-dihydro-quinoline-2-carboxylic acid methyl ester as an off-white powder. MS=527 [M+H]+; MP=191.5-193.1° C.

Workup

  1. customThe reaction mixture was partitioned between EtOAc and water
  2. customthe organic layer separated
  3. extractionthe aqueous layer was extracted with EtOAc (2×25 mL)
  4. washThe combined organic extracts were washed with brine
  5. dry with materialdried over anhydrous Na2SO4
  6. filtrationfiltered
  7. customevaporated under reduced pressure
  8. customThe yellow solid residue was purified by flash chromatography (DCM/MeOH, 90/10)

Sources & evidence

ORD record
ord-ef395a345f8a49c8940aeb236ce54fd3
Source dataset
uspto-grants-2012_04
Patent number
US08163906B2

Reaction notes

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