Trifluoroacetic acid → HCID 57509629, compound

HRID 624110Notes

Reaction equation

HRID 624110 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[CH2:7][N:6]([C:11]([NH:13][C:14]1[CH:38]=[CH:37][C:17]([C:18]([NH:20][CH2:21][C:22]3[CH:36]=[CH:35][C:25]([CH2:26][NH:27]C(=O)OC(C)(C)C)=[CH:24][CH:23]=3)=[O:19])=[CH:16][CH:15]=1)=[O:12])[CH2:5]2.FC(F)(F)C(O)=O>ClCCl>[NH2:27][CH2:26][C:25]1[CH:24]=[CH:23][C:22]([CH2:21][NH:20][C:18]([C:17]2[CH:16]=[CH:15][C:14]([NH:13][C:11]([N:6]3[CH2:5][C:4]4[C:8](=[CH:9][CH:10]=[C:2]([F:1])[CH:3]=4)[CH2:7]3)=[O:12])=[CH:38][CH:37]=2)=[O:19])=[CH:36][CH:35]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 68752324HCID 68752324, compound

Product 1

HCID 57509629HCID 57509629, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

tert-Butyl 4-((4-(5-fluoroisoindoline-2-carboxamido)benzamido)methyl)benzylcarbamate (392 mg, 0.756 mmol) was dissolved in dichloromethane, treated with trifluoroacetic acid (582 μl, 7.56 mmol), stirred for 3 hours at ambient temperature and then concentrated to dryness. The resulting solid was triturated with ether, collected and dried under vacuum to provide the title compound. 1H NMR (400 MHz, DMSO-d6) δ ppm 4.01 (q, J=5.6 Hz, 2H), 4.46 (d, J=6.0 Hz, 2H), 4.76 (d, J=7.9 Hz, 4H), 7.08-7.29 (m, 2H), 7.32-7.44 (m, 5H), 7.67 (d, J=8.7 Hz, 2H), 7.76-7.86 (m, 2H), 8.12 (s, 2H), 8.63 (s, 1H), 8.91 (t, J=6.2 Hz, 1H); MS (ESI(+)) m/e 419 (M+H)+.

Workup

  1. concentrationconcentrated to dryness
  2. customThe resulting solid was triturated with ether
  3. customcollected
  4. customdried under vacuum

Sources & evidence

ORD record
ord-38bec9d4611142f58f5e3d7bd7961071
Source dataset
uspto-grants-2016_04
Patent number
US09302989B2

Reaction notes

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