Trifluoroacetic acid → 3-(8-Chloro-3-methoxy-2,5-dioxo-2,5-dihydro-1H-benzo[b]azepin-4-yl)acrylic Acid

HRID 2257007Notes

Reaction equation

HRID 2257007 reaction equation
C([O:5][C:6]([CH:8]=[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.CO>[Cl:24][C:21]1[CH:22]=[CH:23][C:12]2[C:11](=[O:25])[C:10]([CH:9]=[CH:8][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

5

Reactant 2

HCID 6422Trifluoroacetic acidHCID 540813424-[2-(Tert-butoxycarbonyl)ethenyl]-8-chloro-3-methoxy-2,5-dioxo-2,5-dihydro-1H-benz[b]azepine

Product 1

HCID 538847863-(8-Chloro-3-methoxy-2,5-dioxo-2,5-dihydro-1H-benzo[b]azepin-4-yl)acrylic AcidYield 55.4%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

4-[2-(Tert-butoxycarbonyl)ethenyl]-8-chloro-3-methoxy-2,5-dioxo-2,5-dihydro-1H-benz[b]azepine (0.3455 g) was dissolved in dry methylene chloride (7.5 mL) under argon. The solution was treated with trifluoroacetic acid (7 mL). The solution was stirred at room temperature for 30 minutes. The solution was concentrated under water aspirator vacuum and then it was dried under high vacuum to give a white solid. The solid was dissolved in 125 mL of hot methanol. The solution was filtered and concentrated to 80 mL volume as a white solid formed. It was cooled in an ice bath and the solid was filtered off, washed with cold methanol, and air-dried to give a white solid (0.162 g); mp 281.4°-282.0° C. (dec); 1H NMR (d6 -DMSO) 7.54 (d,1, J=16), 6.52 (d,1, J=16) for trans olefin protons; MS: m/z=308. Analysis for C14H10ClNO5 : Calculated: C, 54.65; H, 3.28; N, 4.55; Found: C, 54.36; H, 3.14; N, 4.37.

Workup

  1. concentrationThe solution was concentrated under water
  2. customit was dried under high vacuum
  3. customto give a white solid
  4. filtrationThe solution was filtered
  5. concentrationconcentrated to 80 mL volume as a white solid
  6. customformed
  7. temperatureIt was cooled in an ice bath
  8. filtrationthe solid was filtered off
  9. washwashed with cold methanol
  10. customair-dried

Sources & evidence

ORD record
ord-8f420b7cb54f41fb9aa553ea33ee7d58
Source dataset
uspto-grants-1997_08
Patent number
US05656626

Reaction notes

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