Trifluoroacetic acid → HCID 18980054, compound

HRID 2257012Notes

Reaction equation

HRID 2257012 reaction equation
C([O:5][C:6]([C:8]([CH3:26])=[CH:9][C:10]1[C:11](=[O:25])[C:12]2[CH:23]=[CH:22][C:21]([Cl:24])=[CH:20][C:13]=2[NH:14][C:15](=[O:19])[C:16]=1[O:17][CH3:18])=[O:7])(C)(C)C.FC(F)(F)C(O)=O>C(Cl)Cl>[Cl:24][C:21]1[CH:22]=[CH:23][C:12]2[C:11](=[O:25])[C:10](/[CH:9]=[C:8](\[CH3:26])/[C:6]([OH:7])=[O:5])=[C:16]([O:17][CH3:18])[C:15](=[O:19])[NH:14][C:13]=2[CH:20]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 54536125HCID 54536125, compound

Product 1

HCID 18980054HCID 18980054, compoundYield 25.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4-[2-(Tert-butoxycarbonyl)propenyl]-8-chloro-3-methyoxy-2,5-dioxo-2,5-dihydro-1H-benz[b]azepine (0.35 g) in methylene chloride (7 mL) was treated with trifluoroacetic acid. The solution was stirred under argon at room temperature for 40 minutes and then it was concentrated to a white solid. The solid was dissolved in hot methanol (30 mL). The solution was filtered and concentrated to 7 mL volume as a solid formed. The solid was filtered off, washed with cold methanol, and air-dried to give a white solid (0.0748 g); mp=277.4°-278.6° C. (dec); 1H NMR (d6 -DMSO) 7.17 (s,1) for olefin proton; MS: m/z=304, 322 (base peak)(M+1). Analysis for C15H12ClNO5 : Calculated: C, 56.00; H, 3.76; N, 4.35; Found: C, 55.86; H, 3.82; N, 4.32.

Workup

  1. concentrationit was concentrated to a white solid
  2. dissolutionThe solid was dissolved in hot methanol (30 mL)
  3. filtrationThe solution was filtered
  4. concentrationconcentrated to 7 mL volume as a solid
  5. customformed
  6. filtrationThe solid was filtered off
  7. washwashed with cold methanol
  8. customair-dried

Sources & evidence

ORD record
ord-d4e77af5b7384fb4a91e4b18c179694b
Source dataset
uspto-grants-1997_08
Patent number
US05656626

Reaction notes

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