Trifluoroacetic acid → HCID 131711067, compound

HRID 2049861Notes

Reaction equation

HRID 2049861 reaction equation
FC(F)(F)C(O)=O.C(O[C:13]([N:15]([CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=1[CH2:24][C:25]([NH:27][CH:28]1[C:54](=[O:55])[N:30]2[C:31]([C:51]([OH:53])=[O:52])=[C:32]([CH2:35][S:36][C:37]3[CH:38]=[CH:39][C:40]4[N:41]([C:43](=[O:50])[N:44]([CH2:46][C:47]([OH:49])=[O:48])[N:45]=4)[N:42]=3)[CH2:33][S:34][C@H:29]12)=[O:26])C)=O)CCC>CCOCC>[CH3:13][NH:15][CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=1[CH2:24][C:25]([NH:27][CH:28]1[C:54](=[O:55])[N:30]2[C:31]([C:51]([OH:53])=[O:52])=[C:32]([CH2:35][S:36][C:37]3[CH:38]=[CH:39][C:40]4[N:41]([C:43](=[O:50])[N:44]([CH2:46][C:47]([OH:49])=[O:48])[N:45]=4)[N:42]=3)[CH2:33][S:34][C@H:29]12)=[O:26]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 131711068HCID 131711068, compound

Product 1

HCID 131711067HCID 131711067, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Trifluoroacetic acid (7 ml.) was added to the t-BOC-derivative 7b (3.8 g., 5.5 m.mole) at 0° C., and the mixture was stirred for 20 minutes at room temperature. Dry ether (100 ml.) was added to the mixture. The resulting precipitate was collected by filtration and washed with dry ether (3×100 ml.). The precipitate was dissolved in a mixture of CH3CN (120 ml.) and water (18 ml.) and the solution was adjusted to pH 5-6 with concentrated NH4OH to give an oily precipitate which was triturated with CH3CN to form solid material. The product 8b was collected by filtration, washed with CH3CN and dried. Yield 2.55 g. (77%).

Workup

  1. filtrationThe resulting precipitate was collected by filtration
  2. washwashed with dry ether (3×100 ml.)
  3. dissolutionThe precipitate was dissolved in a mixture of CH3CN (120 ml.) and water (18 ml.)
  4. customto give an oily precipitate which
  5. customwas triturated with CH3CN
  6. customto form solid material
  7. filtrationThe product 8b was collected by filtration
  8. washwashed with CH3CN
  9. customdried

Sources & evidence

ORD record
ord-80942c3c738f44d28ad5f47f26afd91b
Source dataset
uspto-grants-1980_04
Patent number
US04198506

Reaction notes

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