Trifluoroacetic acid → HCID 56928658, compound

HRID 1772130Notes

Reaction equation

HRID 1772130 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]2[C:11](=[CH:12][CH:13]=1)[C:10](=[O:14])[N:9]([C:15]1[C:16]([CH2:47][OH:48])=[C:17]([C:21]3[CH:22]=[C:23]([NH:29][C:30]4[N:35]=[CH:34][C:33]([CH:36]5[CH2:39][N:38](C(OC(C)(C)C)=O)[CH2:37]5)=[CH:32][CH:31]=4)[C:24](=[O:28])[N:25]([CH3:27])[CH:26]=3)[CH:18]=[CH:19][CH:20]=1)[CH2:8]2)([CH3:4])([CH3:3])[CH3:2].FC(F)(F)C(O)=O>C(Cl)Cl>[NH:38]1[CH2:37][CH:36]([C:33]2[CH:32]=[CH:31][C:30]([NH:29][C:23]3[C:24](=[O:28])[N:25]([CH3:27])[CH:26]=[C:21]([C:17]4[C:16]([CH2:47][OH:48])=[C:15]([N:9]5[CH2:8][C:7]6[C:11](=[CH:12][CH:13]=[C:5]([C:1]([CH3:3])([CH3:4])[CH3:2])[CH:6]=6)[C:10]5=[O:14])[CH:20]=[CH:19][CH:18]=4)[CH:22]=3)=[N:35][CH:34]=2)[CH2:39]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86699868HCID 86699868, compound

Product 1

HCID 56928658HCID 56928658, compoundYield 25%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A 100-mL single-neck round-bottomed flask equipped with a magnetic stirrer was charged with 117e (495 mg, 0.761 mmol), methylene chloride (3 mL) and trifluoroacetic acid (3 mL), and the mixture was stirred at room temperature for 3 h. After this time, the reaction mixture was concentrated, and the resulting residue was partitioned between 10% aqueous potassium carbonate (10 mL) and methylene chloride (20 mL). The layers were separated, and the aqueous phase was extracted with methylene chloride (20 mL). The organic extracts were combined, dried over sodium sulfate and filtered, and the solvent was removed under reduced pressure. The resulting residue was purified by column chromatography to afford a 25% yield (104 mg) of 117 as a white solid: mp 185-186° C.; 1H NMR (500 MHz, DMSO-d6) δ 8.66 (s, 1H), 8.54 (s, 1H), 8.10 (s, 1H), 7.71 (d, 2H, J=8.5 Hz), 7.66 (d, 1H, J=8.5 Hz), 7.61 (d, 1H, J=8.0 Hz), 7.49 (t, 1H, J=8.0 Hz), 7.44 (d, 1H, J=6.5 Hz), 7.37 (m, 2H), 7.28 (d, 1H, J=8.5 Hz), 4.94 (s, 2H), 4.88 (t, 1H, J=4.5 Hz), 4.34 (d, 2H, J=4.5 Hz), 3.71 (m, 3H), 3.59 (s, 3H), 3.54 (m, 2H), 1.33 (s, 9H); MS (ESI+) m/z 550.2 (M+H).

Workup

  1. customA 100-mL single-neck round-bottomed flask equipped with a magnetic stirrer
  2. concentrationAfter this time, the reaction mixture was concentrated
  3. customthe resulting residue was partitioned between 10% aqueous potassium carbonate (10 mL) and methylene chloride (20 mL)
  4. customThe layers were separated
  5. extractionthe aqueous phase was extracted with methylene chloride (20 mL)
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. customthe solvent was removed under reduced pressure
  9. customThe resulting residue was purified by column chromatography

Sources & evidence

ORD record
ord-5bbd603be42b452da74422faa301ff76
Source dataset
uspto-grants-2016_02
Patent number
US09249123B2

Reaction notes

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