Trifluoroacetic acid methylene chloride → HCID 11456638, compound

HRID 908135Notes

Reaction equation

HRID 908135 reaction equation
C(OC(=O)[NH:7][CH2:8][CH2:9][NH:10][C:11]([C:13]1[N:14]([CH3:36])[CH:15]=[C:16]([NH:18][C:19]([C:21]2[N:22]([CH3:35])[CH:23]=[C:24]([NH:26][C:27]([C:29]3[N:30]([CH3:34])[CH:31]=[CH:32][N:33]=3)=[O:28])[CH:25]=2)=[O:20])[CH:17]=1)=[O:12])(C)(C)C.C(O)(C(F)(F)F)=O.C(Cl)Cl>O>[NH2:7][CH2:8][CH2:9][NH:10][C:11]([C:13]1[N:14]([CH3:36])[CH:15]=[C:16]([NH:18][C:19]([C:21]2[N:22]([CH3:35])[CH:23]=[C:24]([NH:26][C:27]([C:29]3[N:30]([CH3:34])[CH:31]=[CH:32][N:33]=3)=[O:28])[CH:25]=2)=[O:20])[CH:17]=1)=[O:12]

Participants

4

Reactant 2

HCID 21863450Trifluoroacetic acid methylene chlorideHCID 67390076HCID 67390076, compound

Product 1

HCID 11456638HCID 11456638, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Compound 6a (0.29 g, 0.06 mmol) and TFA/CH2Cl2 (1:1, 2 ml) containing H2O (40 μl) were stirred at room temperature for 1.5 hr. The solvent was removed under pressure and the residue stirred with DOWEX® 550A OH anion exchange resin (0.05 g, 0.17 mmol, washed with MeOH). The solution was decanted and evaporated. CHCl3 (5 ml) was added and the solid collected and dried under vacuum. Yield 0.02 g (90%). 1H NMR (DMSO): δ 10.49 (s, 1H, NH), 9.96 (s, 1H, NH), 8.13 (t, 1H, NH, J=6.0 Hz) 7.71 (bs, 2H, NH2), 7.40 (d, 1H, J=1.5 Hz), 7.28 (d, 1H, J=1.5 Hz), 7.18 (d, 1H, J=1.5 Hz) 7.15 (d, 1H, J=1.8 Hz), 7.04 (d, 1H, J=1.2 Hz), 6.98 (d, 1H J=1.5 Hz), 3.98 (s, 3H), 3.83 (s, 3H), 3.81 (s, 3H), 3.5-3.2 (m, 2H, CH2), 2.92 (m, 2H, CH2).

Workup

  1. customThe solvent was removed under pressure
  2. stirringthe residue stirred with DOWEX® 550A OH anion exchange resin (0.05 g, 0.17 mmol, washed with MeOH)
  3. customThe solution was decanted
  4. customevaporated
  5. additionCHCl3 (5 ml) was added
  6. customthe solid collected
  7. customdried under vacuum

Sources & evidence

ORD record
ord-e5a93dcf29c84a1098d4b474801b2bb0
Source dataset
uspto-grants-2011_09
Patent number
US08017599B2

Reaction notes

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