Trifluoroacetic acid → HCID 59009206, compound

HRID 545113Notes

Reaction equation

HRID 545113 reaction equation
C(OC([NH:8][NH:9][C:10]([C:12]1[N:13]=[C:14]([S:17][CH2:18][C:19]([NH:21][CH2:22][C@@H:23]2[O:28][CH2:27][CH2:26][N:25]([CH2:29][C:30]3[CH:35]=[CH:34][C:33]([Cl:36])=[C:32]([Cl:37])[CH:31]=3)[CH2:24]2)=[O:20])[S:15][CH:16]=1)=[O:11])=O)(C)(C)C.FC(F)(F)C(O)=O>C(Cl)Cl>[Cl:37][C:32]1[CH:31]=[C:30]([CH:35]=[CH:34][C:33]=1[Cl:36])[CH2:29][N:25]1[CH2:26][CH2:27][O:28][C@@H:23]([CH2:22][NH:21][C:19](=[O:20])[CH2:18][S:17][C:14]2[S:15][CH:16]=[C:12]([C:10]([NH:9][NH2:8])=[O:11])[N:13]=2)[CH2:24]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 67168629HCID 67168629, compound

Product 1

HCID 59009206HCID 59009206, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The resultant product (4.01 g) of (42-1) was dissolved in methylene chloride (30 mL), trifluoroacetic acid (10 mL) was added, and the mixture was stirred overnight. The reaction mixture was concentrated under reduced pressure, a 1 mol/L aqueous sodium hydroxide solution was added to the residue, and the mixture was extracted with chloroform. The extract was washed with saturated brine, dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The obtained residue was recrystallized from a mixed solvent of ethyl acetate and methanol to give the title compound (453 mg) as white crystals.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. additiona 1 mol/L aqueous sodium hydroxide solution was added to the residue
  3. extractionthe mixture was extracted with chloroform
  4. washThe extract was washed with saturated brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. customthe solvent was evaporated under reduced pressure
  7. customThe obtained residue was recrystallized from a mixed solvent of ethyl acetate and methanol

Sources & evidence

ORD record
ord-8c18e64082ae4f99a15f8394e9612147
Source dataset
uspto-grants-2011_05
Patent number
US07935700B2

Reaction notes

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