Trifluoroacetic acid → HCID 11364940, compound

HRID 1766045Notes

Reaction equation

HRID 1766045 reaction equation
C(OC([NH:8][C@H:9]([C:41]1[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1)[CH2:10][N:11]1[C:16](=[O:17])[C:15]([C:18]2[CH:23]=[CH:22][CH:21]=[C:20]([O:24][CH3:25])[C:19]=2[F:26])=[C:14]([CH3:27])[N:13]([CH2:28][C:29]2[C:34]([S:35]([CH3:38])(=[O:37])=[O:36])=[CH:33][CH:32]=[CH:31][C:30]=2[F:39])[C:12]1=[O:40])=O)(C)(C)C.FC(F)(F)C(O)=O>ClCCl>[NH2:8][C@H:9]([C:41]1[CH:42]=[CH:43][CH:44]=[CH:45][CH:46]=1)[CH2:10][N:11]1[C:16](=[O:17])[C:15]([C:18]2[CH:23]=[CH:22][CH:21]=[C:20]([O:24][CH3:25])[C:19]=2[F:26])=[C:14]([CH3:27])[N:13]([CH2:28][C:29]2[C:34]([S:35]([CH3:38])(=[O:37])=[O:36])=[CH:33][CH:32]=[CH:31][C:30]=2[F:39])[C:12]1=[O:40]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86596512HCID 86596512, compound

Product 1

HCID 11364940HCID 11364940, compoundYield 94%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of compound 6c (10 g, 15 mmol) in anhydrous dichloromethane (60 mL) was added trifluroacetic acid (TFA, 16 mL). The reaction mixture was stirred at room temperature for 4 hours. The reaction mixture was concentrated, and partitioned between ethyl acetate and diluted aqueous NaOH solution. The organic layer was washed with saturated aqueous sodium bicarbonate solution and brine, dried with sodium sulfate, filtered and concentrated to yield 6d as a tan solid (8.0 g, 14 mmol, 94%). MS (CI) m/z 556.2 (M+H+), tR=2.354 min. (method 4). 1H NMR (CDCl3): δ 2.25 (s, 3H), 3.42 (s, 1.5H), 3.43 (s, 1.5H), 3.91 (s, 1.5H), 3.92 (s, 1.5H), 3.98–4.22 (m, 2H), 4.33–4.38 (m, 1H), 5.60 (brs, 2H), 6.80–6.89 (m, 1H), 6.97–7.03 (m, 1H), 7.11–7.17 (m, 1H), 7.22–7.37 (m, 6H), 7.46–7.54 (m, 1H), 7.95 (dd, 1H).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. custompartitioned between ethyl acetate and diluted aqueous NaOH solution
  3. washThe organic layer was washed with saturated aqueous sodium bicarbonate solution and brine
  4. dry with materialdried with sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-04f349092453479c971c0e6620179c26
Source dataset
uspto-grants-2007_06
Patent number
US07229995B2

Reaction notes

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