Trifluoroacetic acid → HCID 23597199, compound

HRID 890580Notes

Reaction equation

HRID 890580 reaction equation
[C:1]([S:4][CH2:5][C:6]([NH:8][CH:9]([CH2:24][C:25]([O:27]C(C)(C)C)=[O:26])[C:10](=[O:23])[CH2:11][O:12][C:13](=[O:22])[C:14]1[C:19]([Cl:20])=[CH:18][CH:17]=[CH:16][C:15]=1[Cl:21])=[O:7])(=[O:3])[CH3:2].FC(F)(F)C(O)=O>C(Cl)Cl.CS(C)=O>[C:1]([S:4][CH2:5][C:6]([NH:8][CH:9]([CH2:24][C:25]([OH:27])=[O:26])[C:10](=[O:23])[CH2:11][O:12][C:13](=[O:22])[C:14]1[C:15]([Cl:21])=[CH:16][CH:17]=[CH:18][C:19]=1[Cl:20])=[O:7])(=[O:3])[CH3:2]

Participants

5

Reactant 2

HCID 6422Trifluoroacetic acidHCID 23597198HCID 23597198, compound

Product 1

HCID 23597199HCID 23597199, compound

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

The product 26 was dissolved in 10 ml of dry DCM, cooled to 0° C., and treated with 9 ml trifluoroacetic acid (TFA). The reaction was then removed from the ice bath and allowed to warm to ambient temperature over a period of one hour. Solvent was removed under reduced pressure, and the residue redissoved twice in DCM and evaporated to remove residual TFA. The crude product 13 was purified by reverse-phase high-pressure liquid chromatography to yield 101.9 mg (0.234 mmol, 32% from 25) of white hygroscopic powder. Expected MW=436.37, found 437 (M+1). This was dissolved in dimethylsulfoxide (DMSO) to yield a 50 mM stock solution.

Workup

  1. customThe reaction was then removed from the ice bath
  2. temperatureto warm to ambient temperature over a period of one hour
  3. customSolvent was removed under reduced pressure
  4. customevaporated
  5. customto remove residual TFA
  6. customThe crude product 13 was purified by reverse-phase high-pressure liquid chromatography
  7. customto yield 101.9 mg (0.234 mmol, 32% from 25) of white hygroscopic powder
  8. customto yield a 50 mM stock solution

Sources & evidence

ORD record
ord-26a58d98a1024803b35ac643ac2ef0cf
Source dataset
uspto-grants-2006_02
Patent number
US06998233B2

Reaction notes

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