Trifluoroacetic acid methylene chloride → HCID 58991121, compound

HRID 900552Notes

Reaction equation

HRID 900552 reaction equation
[OH:1][NH:2][C:3]([C@@H:5]([NH:15][C:16]([C:18]1[CH:23]=[CH:22][C:21]([C:24]#[C:25][C:26]2[CH:31]=[CH:30][C:29]([NH:32][C:33](=[O:43])[CH2:34][NH:35]C(OC(C)(C)C)=O)=[CH:28][CH:27]=2)=[CH:20][CH:19]=1)=[O:17])[CH2:6][NH:7]C(OC(C)(C)C)=O)=[O:4].C(O)(C(F)(F)F)=O.C(Cl)Cl>>[NH2:35][CH2:34][C:33]([NH:32][C:29]1[CH:30]=[CH:31][C:26]([C:25]#[C:24][C:21]2[CH:22]=[CH:23][C:18]([C:16]([NH:15][C@@H:5]([CH2:6][NH2:7])[C:3]([NH:2][OH:1])=[O:4])=[O:17])=[CH:19][CH:20]=2)=[CH:27][CH:28]=1)=[O:43]

Participants

3

Reactant 2

HCID 21863450Trifluoroacetic acid methylene chlorideHCID 60126011HCID 60126011, compound

Product 1

HCID 58991121HCID 58991121, compoundYield 104.4%

Procedure

To an oven-dried flask containing N-(4-{2-[4-(N-(1-(N-hydroxycarbamoyl)(1S)-2-[(tert-butoxy)carbonylamino]ethyl}carbamoyl)phenyl]ethynyl}phenyl)-2-[(tert-butoxy)carbonylamino]acetamide (6) (130 mg, 0.218 mmol) was added 1:1 TFA/CH2Cl2 (2.5 mL). The resulting pink solution was stirred for 2 h and concentrated to give a pink gum. The crude residue was rinsed with CH2Cl2 (4 mL), concentrated by rotary evaporation and dissolved in THF (2 mL) and MeOH (0.4 mL). A solution of 4 M HCl in dioxane (200 μL) was added and the resulting precipitate filtered and washed with Et2O (10 mL) to afford 90 mg of 4-({4-[(aminoacetyl)amino]phenyl}ethynyl)-N-[(1S)-1-(aminomethyl)-2-(hydroxyamino)-2-oxoethyl]benzamide as a pale tan powder.

Workup

  1. concentrationconcentrated
  2. customto give a pink gum
  3. washThe crude residue was rinsed with CH2Cl2 (4 mL)
  4. concentrationconcentrated by rotary evaporation
  5. dissolutiondissolved in THF (2 mL)
  6. additionA solution of 4 M HCl in dioxane (200 μL) was added
  7. filtrationthe resulting precipitate filtered
  8. washwashed with Et2O (10 mL)

Sources & evidence

ORD record
ord-62fb370b70174919ad9b4533f1576f62
Source dataset
uspto-grants-2008_04
Patent number
US07358359B2

Reaction notes

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