Trifluoroacetic acid → Trifluoroacetic acid

HRID 605098Notes

Reaction equation

HRID 605098 reaction equation
C([O:8][C:9]1[CH:45]=[CH:44][C:12]([O:13][C:14]2[CH:29]=[CH:28][C:17]([C:18]([NH:20][C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=3[F:27])=[O:19])=[CH:16][C:15]=2[NH:30][C:31]2[C:32]3[CH:40]=[CH:39][C:38]([CH:41]([CH3:43])[CH3:42])=[N:37][C:33]=3[N:34]=[CH:35][N:36]=2)=[CH:11][CH:10]=1)C1C=CC=CC=1.CC1C(C)=C(C)C(C)=C(C)C=1.[F:57][C:58]([F:63])([F:62])[C:59]([OH:61])=[O:60]>>[F:27][C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][C:21]=1[NH:20][C:18](=[O:19])[C:17]1[CH:28]=[CH:29][C:14]([O:13][C:12]2[CH:11]=[CH:10][C:9]([OH:8])=[CH:45][CH:44]=2)=[C:15]([NH:30][C:31]2[C:32]3[CH:40]=[CH:39][C:38]([CH:41]([CH3:42])[CH3:43])=[N:37][C:33]=3[N:34]=[CH:35][N:36]=2)[CH:16]=1.[F:57][C:58]([F:63])([F:62])[C:59]([OH:61])=[O:60]

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 12784PentamethylbenzeneHCID 67040494HCID 67040494, compound

Product 2

HCID 6422Trifluoroacetic acidYield 22%HCID 67040842HCID 67040842, compound

Procedure

A solution of the product of Example 43E and pentamethylbenzene (72 mg, 0.5 mmol) in trifluoroacetic acid (5 mL) was stirred at room temperature for 1 hour. The solvent was removed by rotary evaporation under vacuum and co-evaporated with methylene chloride/hexanes (2×) to provide the crude title compound which was purified by HPLC with TFA to provide the title compound as a trifluoroacetic acid salt (11 mg, 22%). 1H NMR (300 MHz, DMSO-D6) δ ppm: 1.34 (d, J=6.62 Hz, 6 H) 3.28 (m, 1 H) 6.77 (m, 2 H) 6.93 (m, 3 H) 7.26 (m, 3 H) 7.58 (m, 1 H) 7.88 (d, J=8.82 z, 1 H) 8.00 (dd, J=8.64, 2.02 Hz, 1 H) 8.14 (d, J=2.21 Hz, 1 H) 8.91 (s, 1 H) 9.00 (d, J=8.09 Hz, 1 H) 9.47 (s, 1 H) 10.13 (s, 1 H) 11.48 (s, 1 H); MS (ESI+) m/z 510 (M+H)+.

Workup

  1. customThe solvent was removed by rotary evaporation under vacuum and co-evaporated with methylene chloride/hexanes (2×)
  2. customto provide the crude title compound which
  3. customwas purified by HPLC with TFA

Sources & evidence

ORD record
ord-f77d5d3b75f548d3a08c13b9ff5fe212
Source dataset
uspto-grants-2011_03
Patent number
US07910595B2

Reaction notes

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