Trifluoroacetic acid → HCID 86645553, compound

HRID 444614Notes

Reaction equation

HRID 444614 reaction equation
[C:1]1([CH3:44])[CH:6]=[CH:5][C:4]([O:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][NH:19][C:20](=[O:43])[CH2:21][CH2:22][S:23]C(C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=[CH:3][CH:2]=1.FC(F)(F)C(O)=O.C([SiH](CC)CC)C>C(Cl)Cl>[C:1]1([CH3:44])[CH:2]=[CH:3][C:4]([O:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][NH:19][C:20](=[O:43])[CH2:21][CH2:22][SH:23])=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 67541218HCID 67541218, compound

Product 1

HCID 86645553HCID 86645553, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

The compound 25 (0.181 g) was dissolved in 1 ml of methylene chloride, and 0.5 ml of trifluoroacetic acid was added to that while being stirred, to obtain a brown-colored solution. After a white-colored precipitate was generated by adding 0.16 ml of triethylsilane, the supernatant solution was distilled away under reduced pressure. The solid obtained was dissolved by the new addition of 20 ml of methylene chloride, and was washed twice with 30 ml of aqueous saturated sodium hydrogen carbonate solution and twice with 30 ml of saturated brine. After the collected organic phase was dehydrated with magnesium sulfate, the desiccant agent was removed by filtration, and the solvent of the filtrate was distilled away under reduced pressure. The reaction mixture was purified by chromatography, and 0.1 g of the compound f, which was a white solid, was obtained.

Workup

  1. customto obtain a brown-colored solution
  2. distillationthe supernatant solution was distilled away under reduced pressure
  3. customThe solid obtained
  4. washwas washed twice with 30 ml of aqueous saturated sodium hydrogen carbonate solution and twice with 30 ml of saturated brine
  5. customthe desiccant agent was removed by filtration
  6. distillationthe solvent of the filtrate was distilled away under reduced pressure
  7. customThe reaction mixture was purified by chromatography, and 0.1 g of the compound f, which
  8. customwas obtained

Sources & evidence

ORD record
ord-cbb85f9e648a4b26ab9e7353822979bb
Source dataset
uspto-grants-2013_07
Patent number
US08475685B2

Reaction notes

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