Trifluoroacetic acid → HCID 23369751, compound

HRID 1900766Notes

Reaction equation

HRID 1900766 reaction equation
C(O[C:6]([N:8](C)[CH2:9][C:10]([NH:12][CH2:13][CH:14]1[O:28][C:17]2=[C:18]3[C:23](=[C:24]([CH3:26])[CH:25]=[C:16]2[CH2:15]1)[NH:22][C:21](=[O:27])[CH:20]=[CH:19]3)=[O:11])=O)(C)(C)C.FC(F)(F)C(O)=O>>[CH3:6][NH:8][CH2:9][C:10]([NH:12][CH2:13][CH:14]1[O:28][C:17]2=[C:18]3[C:23](=[C:24]([CH3:26])[CH:25]=[C:16]2[CH2:15]1)[NH:22][C:21](=[O:27])[CH:20]=[CH:19]3)=[O:11]

Participants

3

Reactant 2

HCID 6422Trifluoroacetic acidHCID 23369814HCID 23369814, compound

Product 1

HCID 23369751HCID 23369751, compoundYield 96.2%

Procedure

The compound obtained in Example 232 (2.75 g, 6.9 mmol) was added to trifluoroacetic acid (15 ml) under cooling conditions, and the mixture was stirred for 30 minutes. The reaction mixture was subjected to distillation under reduced pressure, and the residue was purified by silica gel column chromatography (chloroform: methanol =3:1). The obtained crystals were dissolved in chloroform-methanol (3:1, 20 ml), and 5% HCl-methanol (10 ml) was added thereto while cooling on ice. The mixture was condensed under reduced pressure. The resultant residue was recrystallized from methanol--ether. 2.0 g of the title compound was obtained as pale yellow crystals (86.0%).

Workup

  1. distillationThe reaction mixture was subjected to distillation under reduced pressure
  2. customthe residue was purified by silica gel column chromatography (chloroform: methanol =3:1)
  3. dissolutionThe obtained crystals were dissolved in chloroform-methanol (3:1, 20 ml)
  4. addition5% HCl-methanol (10 ml) was added
  5. temperaturewhile cooling on ice
  6. customcondensed under reduced pressure
  7. customThe resultant residue was recrystallized from methanol

Sources & evidence

ORD record
ord-132ef7f39fda498b980fc02e9f9e1cad
Source dataset
uspto-grants-1996_11
Patent number
US05576324

Reaction notes

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