Trifluoroacetic acid → HCID 15542647, compound

HRID 379005Notes

Reaction equation

HRID 379005 reaction equation
C([O:5][CH2:6][C@@H:7]([CH3:51])[C:8]([NH:10][C:11]1[CH:16]=[CH:15][C:14]([C:17]2[S:40][C:20]3[N:21]([CH2:31][C:32]4[C:37]([F:38])=[CH:36][CH:35]=[CH:34][C:33]=4[F:39])[CH:22]=[C:23]([C:26](=[O:30])[CH:27]([CH3:29])[CH3:28])[C:24](=[O:25])[C:19]=3[C:18]=2[CH2:41][N:42]([CH2:44][C:45]2[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=2)[CH3:43])=[CH:13][CH:12]=1)=[O:9])(C)(C)C.FC(F)(F)C(O)=O>>[OH:5][CH2:6][C@@H:7]([CH3:51])[C:8]([NH:10][C:11]1[CH:12]=[CH:13][C:14]([C:17]2[S:40][C:20]3[N:21]([CH2:31][C:32]4[C:37]([F:38])=[CH:36][CH:35]=[CH:34][C:33]=4[F:39])[CH:22]=[C:23]([C:26](=[O:30])[CH:27]([CH3:28])[CH3:29])[C:24](=[O:25])[C:19]=3[C:18]=2[CH2:41][N:42]([CH2:44][C:45]2[CH:46]=[CH:47][CH:48]=[CH:49][CH:50]=2)[CH3:43])=[CH:15][CH:16]=1)=[O:9]

Participants

3

Reactant 2

HCID 6422Trifluoroacetic acidHCID 15542652HCID 15542652, compound

Product 1

HCID 15542647HCID 15542647, compoundYield 6.7%

Procedure

The compound obtained in Example 9 (11.11 g) was dissolved trifluoroacetic acid (5 ml) under ice cooling conditions, and then after stirring for 1 hour, the solution was allowed to warm to room temperature and stirred for further 12 hours. The reaction mixture was concentrated to dryness under reduced pressure, and then the residue was dissolved in methanol (20 ml) and again cooled with ice, and then a 5 N solution of sodium hydroxide was added to reach pH 9.0. The reaction mixture was stirred for 30 minutes and further stirred at room temperature for 30 minutes. The reaction mixture was concentrated to dryness under reduced pressure at low temperature, and then the obtained residue was chromatographed on silica gel. The light yellow amorphous crystals obtained (0.83 g, 82%) were recrystallized from ether to yield light yellow powdery crystals (0.69 g).

Workup

  1. stirringstirred for further 12 hours
  2. concentrationThe reaction mixture was concentrated to dryness under reduced pressure
  3. dissolutionthe residue was dissolved in methanol (20 ml)
  4. temperatureagain cooled with ice
  5. additiona 5 N solution of sodium hydroxide was added
  6. stirringThe reaction mixture was stirred for 30 minutes
  7. stirringfurther stirred at room temperature for 30 minutes
  8. concentrationThe reaction mixture was concentrated to dryness under reduced pressure at low temperature
  9. customthe obtained residue was chromatographed on silica gel
  10. customThe light yellow amorphous crystals obtained (0.83 g, 82%)
  11. customwere recrystallized from ether

Sources & evidence

ORD record
ord-d41154ee5e5740d0971e58a8db52b71b
Source dataset
uspto-grants-2001_10
Patent number
US06297255B1

Reaction notes

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