Trifluoroacetic acid → HCID 52914146, compound

HRID 531165Notes

Reaction equation

HRID 531165 reaction equation
[C:1]([CH2:8][N:9]1[CH2:22][CH2:21][CH2:20][N:19]2[CH2:23][CH:24]([CH2:26][C:27]3[CH:32]=[CH:31][C:30]([N+:33]([O-])=O)=[CH:29][CH:28]=3)[CH2:25][N:12]([CH2:13][CH2:14][CH2:15][N:16]([CH2:36][C:37]([O:39]C(C)(C)C)=[O:38])[CH2:17][CH2:18]2)[CH2:11][CH2:10]1)([O:3]C(C)(C)C)=[O:2].C(O)(C(F)(F)F)=O>C(O)C.[Pd]>[C:1]([CH2:8][N:9]1[CH2:22][CH2:21][CH2:20][N:19]2[CH2:23][CH:24]([CH2:26][C:27]3[CH:28]=[CH:29][C:30]([NH2:33])=[CH:31][CH:32]=3)[CH2:25][N:12]([CH2:13][CH2:14][CH2:15][N:16]([CH2:36][C:37]([OH:39])=[O:38])[CH2:17][CH2:18]2)[CH2:11][CH2:10]1)([OH:3])=[O:2]

Participants

5

Reactant 2

HCID 6422Trifluoroacetic acidHCID 52914148HCID 52914148, compound

Product 1

HCID 52914146HCID 52914146, compoundYield 145.7%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a solution of 51 (0.42 g, 0.58 mmol) in ethanol (50 mL) was added 10% Pd/C (0.13 g). The resulting mixture was stirred under H2 (g) atmosphere at room temperature for 12 hours. The reaction mixture was filtered through a celite pad and washed with ethanol (2×20 mL). The combined filtrate was evaporated under vacuum to give an oily residue which was triturated with Et2O to provide yellow solid 28 (0.39 g, 98% yield) (2 equiv TFA calculated on the basis of mass).

Workup

  1. filtrationThe reaction mixture was filtered through a celite pad
  2. washwashed with ethanol (2×20 mL)
  3. customThe combined filtrate was evaporated under vacuum
  4. customto give an oily residue which
  5. customwas triturated with Et2O

Sources & evidence

ORD record
ord-b24081869d7a4090b4a5747fd8fc6f1b
Source dataset
uspto-grants-2016_05
Patent number
US09353120B2

Reaction notes

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