Trifluoroacetic acid → HCID 25181460, compound

HRID 1942802Notes

Reaction equation

HRID 1942802 reaction equation
[F:1][C:2]1[CH:36]=[C:35]([NH:37][C:38]([NH:40][C:41]2[CH:45]=[C:44]([CH3:46])[O:43][N:42]=2)=[O:39])[CH:34]=[CH:33][C:3]=1[O:4][C:5]1[CH:10]=[CH:9][N:8]=[C:7]2[CH:11]=[C:12]([C:14]3[N:19]=[CH:18][C:17]([CH2:20][N:21]([CH2:29][CH2:30][O:31][CH3:32])C(=O)OC(C)(C)C)=[CH:16][CH:15]=3)[S:13][C:6]=12.C(O)(C(F)(F)F)=O>ClCCl>[F:1][C:2]1[CH:36]=[C:35]([NH:37][C:38]([NH:40][C:41]2[CH:45]=[C:44]([CH3:46])[O:43][N:42]=2)=[O:39])[CH:34]=[CH:33][C:3]=1[O:4][C:5]1[CH:10]=[CH:9][N:8]=[C:7]2[CH:11]=[C:12]([C:14]3[CH:15]=[CH:16][C:17]([CH2:20][NH:21][CH2:29][CH2:30][O:31][CH3:32])=[CH:18][N:19]=3)[S:13][C:6]=12

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 57919521HCID 57919521, compound

Product 1

HCID 25181460HCID 25181460, compoundYield 45%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To compound 148 (0.27 g, 0.42 mmol) in dichloromethane (75 mL) was added TFA (3 mL). The solution was stirred for 18 h then concentrated. The residue was partitioned between dichloromethane and 1M NaOH, and filtered to remove insolubles. The organic phase was collected, washed with 1M NaOH, brine, dried (anhydrous MgSO4), filtered, and concentrated. The residue was triturated with ether to afford title compound 149 (0.10 g, 45% yield). 1H NMR (400 MHz, DMSO-d6) δ (ppm): 9.67 (s, 1H), 9.23 (s, 1H), 8.56 (d, J=1.4 Hz, 1H), 8.51 (d, J=5.3 Hz, 1H), 8.31 (s, 1H), 8.22 (d, J=8.0 Hz, 1H), 7.88 (dd, J=8.0, 2.0 Hz, 1H), 7.73 (dd, J=12.9, 2.3 Hz, 1H), 7.46 (t, J=9.0 Hz, 1H), 7.29-7.26 (m, 1H), 6.65 (d, J=5.5 Hz, 1H), 6.55 (s, 1H), 3.77 (s, 2H), 3.40 (t, J=5.7 Hz, 2H), 3.23 (s, 3H), 2.64 (t, J=5.7 Hz, 2H), 2.36 (s, 3H). MS (m/z): 549.1 (M+H).

Workup

  1. concentrationthen concentrated
  2. customThe residue was partitioned between dichloromethane and 1M NaOH
  3. filtrationfiltered
  4. customto remove insolubles
  5. customThe organic phase was collected
  6. washwashed with 1M NaOH, brine
  7. dry with materialdried (anhydrous MgSO4)
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customThe residue was triturated with ether

Sources & evidence

ORD record
ord-c6041683a32d4d43bba265b935995abd
Source dataset
uspto-grants-2013_03
Patent number
US08389541B2

Reaction notes

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