Trifluoroacetic acid → HCID 86608880, compound

HRID 1782194Notes

Reaction equation

HRID 1782194 reaction equation
[Cl:1][CH:2]([Cl:35])[C:3]([N:5]([CH2:25][CH2:26][NH:27]C(=O)OC(C)(C)C)[C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([C:12]2[O:16][N:15]=[C:14]([C:17]3[C:22]([Cl:23])=[CH:21][CH:20]=[CH:19][C:18]=3[Cl:24])[CH:13]=2)[CH:7]=1)=[O:4].[F:36][C:37]([F:42])([F:41])[C:38]([OH:40])=[O:39]>ClCCl>[F:36][C:37]([F:42])([F:41])[C:38]([OH:40])=[O:39].[NH2:27][CH2:26][CH2:25][N:5]([C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([C:12]2[O:16][N:15]=[C:14]([C:17]3[C:22]([Cl:23])=[CH:21][CH:20]=[CH:19][C:18]=3[Cl:24])[CH:13]=2)[CH:7]=1)[C:3](=[O:4])[CH:2]([Cl:1])[Cl:35]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 57588411HCID 57588411, compound

Product 1

HCID 86608880HCID 86608880, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

tert-butyl 2-(2,2-dichloro-N-(3-(3-(2,6-dichlorophenyl)isoxazol-5-yl)phenyl)acetamido)ethylcarbamate (100 mg, 0.18 mmol) was dissolved in anhydrous dichloromethane (3 mL) and cooled in an ice-bath under nitrogen. Then trifluoroacetic acid (3 mL) was added. After 3 h at 4° C. the mixture was concentrated under reduced pressure. The residue was dissolved and concentrated under reduced pressure again to give N-(2-aminoethyl)-2,2-dichloro-N-(3-(3-(2,6-dichlorophenyl)isoxazol-5-yl)phenyl)acetamide trifluoroacetate salt as a white solid. 1H NMR (CDCl3): 8.04 (s, 1H), 7.65-7.62 (m, 2H), 7.43-7.30 (m, 4H), 6.73 (s, 1H), 5.95 (s, 1H), 4.21 (m, 2H), 3.35 ppm (m, 2H).

Workup

  1. temperaturecooled in an ice-bath under nitrogen
  2. concentrationAfter 3 h at 4° C. the mixture was concentrated under reduced pressure
  3. dissolutionThe residue was dissolved
  4. concentrationconcentrated under reduced pressure again

Sources & evidence

ORD record
ord-ad392387124d414bb3c5f5899dd40bc6
Source dataset
uspto-grants-2009_03
Patent number
US07498353B2

Reaction notes

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