Trifluoroacetic acid → HCID 11767389, compound

HRID 1596049Notes

Reaction equation

HRID 1596049 reaction equation
[F:1][C:2]([F:49])([F:48])[O:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[CH:15]=[CH:14][C:13]([S:16]([N:19]([CH2:30][C:31]3[CH:40]=[CH:39][C:38]4[C:33](=[CH:34][CH:35]=[CH:36][CH:37]=4)[C:32]=3[C:41]([O:43]C(C)(C)C)=[O:42])[C:20]([O:22][CH2:23][C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)=[O:21])(=[O:18])=[O:17])=[CH:12][CH:11]=2)=[CH:6][CH:5]=1.FC(F)(F)C(O)=O>C(Cl)Cl>[F:49][C:2]([F:1])([F:48])[O:3][C:4]1[CH:5]=[CH:6][C:7]([C:10]2[CH:11]=[CH:12][C:13]([S:16]([N:19]([CH2:30][C:31]3[CH:40]=[CH:39][C:38]4[C:33](=[CH:34][CH:35]=[CH:36][CH:37]=4)[C:32]=3[C:41]([OH:43])=[O:42])[C:20]([O:22][CH2:23][C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)=[O:21])(=[O:18])=[O:17])=[CH:14][CH:15]=2)=[CH:8][CH:9]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 10996063HCID 10996063, compound

Product 1

HCID 11767389HCID 11767389, compoundYield 100.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

A solution of Example 9F (1.19 g, 1.72 mmol) in CH2Cl2 (35 mL) under N2 at −20° C. was treated with trifluoroacetic acid (13.3 mL, 0.172 mol) and allowed to stir at 0° C. 2 for 1 hour and then quenched with 2.6 M Na2CO3 (50 mL). The reaction mixture was reacidified to pH 3 with 1 M aq HCl, extracted with ethyl acetate. The combined ogranic layers were washed with brine, dried (Na2SO4), filtered, and concentrated (chasing with anhydrous toluene) to provide 1.096 g (100%) of the desired compound white powder.

Workup

  1. customquenched with 2.6 M Na2CO3 (50 mL)
  2. extractionextracted with ethyl acetate
  3. washThe combined ogranic layers were washed with brine
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated (chasing with anhydrous toluene)

Sources & evidence

ORD record
ord-2b01e8916fd3492084360ede59d7651f
Source dataset
uspto-grants-2001_09
Patent number
US06288261B1

Reaction notes

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