Trifluoroacetic acid → HCID 68093200, compound

HRID 1778370Notes

Reaction equation

HRID 1778370 reaction equation
C(O)(C(F)(F)F)=O.[CH2:8]([NH:10][CH2:11]/[CH:12]=[CH:13]\[C:14]1[CH:19]=[C:18]([F:20])[CH:17]=[CH:16][C:15]=1[S:21]([N:24]([C:33]1[C:42]([C:43]([O:45][CH3:46])=[O:44])=[C:41]2[C:36]([C:37]3[CH:49]=[CH:48][O:47][C:38]=3[CH2:39][O:40]2)=[CH:35][CH:34]=1)COCC[Si](C)(C)C)(=[O:23])=[O:22])[CH3:9].C(=O)([O-])[O-].[K+].[K+]>C(Cl)Cl>[CH2:8]([NH:10][CH2:11]/[CH:12]=[CH:13]\[C:14]1[CH:19]=[C:18]([F:20])[CH:17]=[CH:16][C:15]=1[S:21]([NH:24][C:33]1[C:42]([C:43]([O:45][CH3:46])=[O:44])=[C:41]2[C:36]([C:37]3[CH:49]=[CH:48][O:47][C:38]=3[CH2:39][O:40]2)=[CH:35][CH:34]=1)(=[O:23])=[O:22])[CH3:9]

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 11430Potassium CarbonateHCID 66692817HCID 66692817, compound2×

Product 1

HCID 68093200HCID 68093200, compoundYield 29.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

TFA (1 mL) was added to a solution of methyl 7-{N-[2-((Z)-3-ethylaminoprop-1-enyl)-4-fluorobenzenesulfonyl]-N-(2-trimethylsilanylethoxymethyl)-amino}-furo[2,3-c]chromene-6-carboxylate (Intermediate 47, 0.410 g) in DCM (10 mL). The reaction mixture was stirred at room temperature for 30 minutes. Aqueous potassium carbonate was added and the layers were separated. The organic layer was dried (Na2SO4), filtered and the filtrate was concentrated in vacuo. The residue was purified by chromatography on silica, eluting with DMAW 350, followed by DMAW 240 to give methyl 7-[2-((Z)-3-ethylaminoprop-1-enyl)-4-fluorobenzenesulfonylamino]-4H-furo[2,3-c]chromene-6-carboxylate (0.096 g) as a yellow gum.

Workup

  1. customthe layers were separated
  2. dry with materialThe organic layer was dried (Na2SO4)
  3. filtrationfiltered
  4. concentrationthe filtrate was concentrated in vacuo
  5. customThe residue was purified by chromatography on silica
  6. washeluting with DMAW 350

Sources & evidence

ORD record
ord-ee368fcebecd4ff0b9ec704ff99d2e2c
Source dataset
uspto-grants-2016_02
Patent number
US09266896B2

Reaction notes

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