Trifluoroacetic acid → HCID 72836007, compound

HRID 1790256Notes

Reaction equation

HRID 1790256 reaction equation
C(OC([NH:8][CH:9]([CH2:14][C:15]1[CH:20]=[CH:19][C:18]([O:21][CH2:22][CH2:23][N:24]2[C:28]3[CH:29]=[CH:30][C:31]([C:33](=[N:40][O:41][CH3:42])[C:34]4[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=4)=[CH:32][C:27]=3[S:26][C:25]2=[O:43])=[CH:17][CH:16]=1)[C:10]([O:12][CH3:13])=[O:11])=O)(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[NH2:8][CH:9]([CH2:14][C:15]1[CH:20]=[CH:19][C:18]([O:21][CH2:22][CH2:23][N:24]2[C:28]3[CH:29]=[CH:30][C:31]([C:33](=[N:40][O:41][CH3:42])[C:34]4[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=4)=[CH:32][C:27]=3[S:26][C:25]2=[O:43])=[CH:17][CH:16]=1)[C:10]([O:12][CH3:13])=[O:11]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 72977406HCID 72977406, compound

Product 1

HCID 72836007HCID 72836007, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Dissolve the compound obtained in Example 10 (1 eq.) in 250 ml of anhydrous DCM and add TFA (20 eq.) dropwise. Stir for 5 hours and evaporate. Take up in water and render alkaline using 10% K2CO3. Extract with ethyl acetate. Wash the organic phases with water, dry over MgSO4, filter and evaporate. Take up in a minimum of methanol and bubble HCl gas through the mixture for 30 minutes. Evaporate to dryness and take up in diisopropyl ether. Filter off the precipitate and recrystallise from diethyl ether.

Workup

  1. customevaporate
  2. extractionExtract with ethyl acetate
  3. washWash the organic phases with water
  4. dry with materialdry over MgSO4
  5. filtrationfilter
  6. customevaporate
  7. custombubble HCl gas through the mixture for 30 minutes
  8. customEvaporate to dryness
  9. filtrationFilter off the precipitate
  10. customrecrystallise from diethyl ether

Sources & evidence

ORD record
ord-909429328f9c43f0b3f4f7598de5461c
Source dataset
uspto-grants-2006_07
Patent number
US07071221B2

Reaction notes

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