Trifluoroacetic acid → HCID 131711067, compound

HRID 26999Notes

Reaction equation

HRID 26999 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-823cbf5db8014303b414019cb39647d9
Source dataset
uspto-grants-1979_04
Patent number
US04151352

Reaction notes

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