Trifluoroacetic acid → HCID 24875148, compound

HRID 2264722Notes

Reaction equation

HRID 2264722 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([C:8]2([C:25]3[CH:30]=[CH:29][C:28]([O:31][S:32]([CH3:35])(=[O:34])=[O:33])=[CH:27][CH:26]=3)[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[C:10]([NH:17]C(OC(C)(C)C)=O)=[N:9]2)[CH:5]=[CH:6][CH:7]=1.[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].[NH2:17][C:10]1[C:11]2[C:16](=[CH:15][CH:14]=[CH:13][CH:12]=2)[C:8]([C:25]2[CH:30]=[CH:29][C:28]([O:31][S:32]([CH3:35])(=[O:34])=[O:33])=[CH:27][CH:26]=2)([C:4]2[CH:5]=[CH:6][CH:7]=[C:2]([Br:1])[CH:3]=2)[N:9]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 59596285HCID 59596285, compound

Product 1

HCID 24875148HCID 24875148, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To methanesulfonic acid 4-[1-(3-bromo-phenyl)-3-tert-butoxycarbonylamino-1H-isoindol-1-yl]-phenyl ester (Scheme #6, T) (730 mg, 1.31 mmol) was added 10% trifluoroacetic acid in dichloromethane (10 mL) and the reaction stirred 30 minutes. The solvents were removed under reduced pressure and the resulting oil put under high vacuum. Ether, 20 mL, was added to the gum and the solvent removed under reduced pressure giving the title compound (671 mg, 90%). 1H NMR (500 MHz, DMSO-d6) δ 8.32 (d, J=7.9 Hz, 1 H), 7.90-7.86 (m, 2 H), 7.76 (ddd, J=7.9, 6.1, 2.0 Hz, 1 H), 7.63 (d, J=8.0 Hz, 1 H), 7.46 (t, J=1.8 Hz, 1 H), 7.41-7.35 (m, 5 H), 7.31 (d, J=8.5 Hz, 1 H), 3.40 (d, J=4.0 Hz, 3 H); MS (ES+) m/z 457 [M+1]+; tR=1.84 min.

Workup

  1. customThe solvents were removed under reduced pressure
  2. additionEther, 20 mL, was added to the gum
  3. customthe solvent removed under reduced pressure

Sources & evidence

ORD record
ord-0a6f00469ae44cf3bbec4fe2868a861f
Source dataset
uspto-grants-2010_12
Patent number
US07855213B2

Reaction notes

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