Trifluoroacetic acid → HCID 60111017, compound

HRID 2252467Notes

Reaction equation

HRID 2252467 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([O:8][CH2:9][CH2:10][CH2:11][C:12](=[O:27])[NH:13][CH2:14][CH2:15][NH:16]C(OCC2C=CC=CC=2)=O)[CH:5]=[C:4]([CH3:28])[C:3]=1[S:29]([NH:32][C@@H:33]([CH2:38][NH:39][C:40]([C:42]1[CH:50]=[C:49]2[C:45]([C:46]([CH2:52][CH2:53][CH2:54][NH:55][C:56]3[CH:61]=[CH:60][CH:59]=[CH:58][N:57]=3)=[N:47][N:48]2[CH3:51])=[CH:44][CH:43]=1)=[O:41])[C:34]([O:36][CH3:37])=[O:35])(=[O:31])=[O:30].FC(F)(F)C(O)=O>CO.[Pd]>[NH2:16][CH2:15][CH2:14][NH:13][C:12]([CH2:11][CH2:10][CH2:9][O:8][C:6]1[CH:5]=[C:4]([CH3:28])[C:3]([S:29]([NH:32][C@@H:33]([CH2:38][NH:39][C:40]([C:42]2[CH:50]=[C:49]3[C:45]([C:46]([CH2:52][CH2:53][CH2:54][NH:55][C:56]4[CH2:61][CH2:60][CH2:59][CH2:58][N:57]=4)=[N:47][N:48]3[CH3:51])=[CH:44][CH:43]=2)=[O:41])[C:34]([O:36][CH3:37])=[O:35])(=[O:30])=[O:31])=[C:2]([CH3:1])[CH:7]=1)=[O:27]

Participants

5

Reactant 2

HCID 6422Trifluoroacetic acidHCID 60111033HCID 60111033, compound

Product 1

HCID 60111017HCID 60111017, compoundYield 116.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent2×

Procedure

In a Parr bottle were added 10% Pd/C (50 mg) and methanol (5 mL) under nitrogen. The product of Step A (113 mg, 116 umol) in methanol (5 mL) was added, along with 20 uL of trifluoroacetic acid. The mixture was hydrogenated at 50 psi with shaking for 7.5 hours, filtered through Celite, the Celite rinsed with methanol, and the combined filtrates concentrated. The residue was redissolved in 1:1 acetonitrile/water/0.1% TFA, frozen and lyophilized to afford the product as a white powder (98 mg, 88%).

Workup

  1. filtrationfiltered through Celite
  2. washthe Celite rinsed with methanol
  3. concentrationthe combined filtrates concentrated
  4. dissolutionThe residue was redissolved in 1:1 acetonitrile/water/0.1% TFA
  5. temperaturefrozen

Sources & evidence

ORD record
ord-54281219b26f4d6d8653cf907c722558
Source dataset
uspto-grants-2008_01
Patent number
US07321045B2

Reaction notes

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