Trifluoroacetic acid → HCID 24999908, compound

HRID 747653Notes

Reaction equation

HRID 747653 reaction equation
O=[N+]([O-])[O-].[O-][N+](=O)[O-].[O-][N+](=O)[O-].[O-][N+](=O)[O-].[O-][N+](=O)[O-].[O-][N+](=O)[O-].[Ce+4].[NH4+].[NH4+].[CH2:28]([O:30][C:31]([C:33]1[CH:38]([C:39]2[CH:44]=[CH:43][C:42]([C:45](=[O:54])[NH:46][CH2:47][C:48]3[CH:49]=[N:50][CH:51]=[CH:52][CH:53]=3)=[CH:41][CH:40]=2)[C:37]([C:55](=[O:57])[NH2:56])=[C:36]([CH2:58][CH:59]([CH3:61])[CH3:60])[NH:35][C:34]=1[CH2:62][CH2:63][C:64]1[CH:69]=[CH:68][C:67]([F:70])=[CH:66][CH:65]=1)=[O:32])[CH3:29].FC(F)(F)C(O)=O>C(Cl)(Cl)Cl>[CH2:28]([O:30][C:31](=[O:32])[C:33]1[C:38]([C:39]2[CH:44]=[CH:43][C:42]([C:45](=[O:54])[NH:46][CH2:47][C:48]3[CH:49]=[N:50][CH:51]=[CH:52][CH:53]=3)=[CH:41][CH:40]=2)=[C:37]([C:55](=[O:57])[NH2:56])[C:36]([CH2:58][CH:59]([CH3:61])[CH3:60])=[N:35][C:34]=1[CH2:62][CH2:63][C:64]1[CH:69]=[CH:68][C:67]([F:70])=[CH:66][CH:65]=1)[CH3:29]

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 180504Ceric ammonium nitrateHCID 59749717HCID 59749717, compound

Product 1

HCID 24999908HCID 24999908, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

An aqueous solution of CAN (1 M, 1 mL) was added to a solution of compound 12 (50 mg, 0.08 mmol) and trifluoroacetic acid (0.5 mL) in CHCl3 (30 mL). The resulting mixture was vigorously stirred for 10 min at r.t. The organic layer was separated, washed with water, dried over Na2SO4, and concentrated in vacuo to yield the crude product. Purification by preparative LCMS (PE SCIEX, C18, acetonitrile—water with 0.035% trifluoroacetic acid) yielded the title compound (2.6 mg, 95% purity by LCMS). 1H NMR (500 MHz, CDCl3): δ 8.16 (s, 1H), 8.00 (br. d, 1H), 7.87 (m, 3H), 7.35 (m, 2H), 7.18 (d, J=8.5 Hz, 1H), 7.08 (m, 2H), 6.90 (m, 2H), 6.03 (br. s, 1H), 5.60 (br. s, 1H), 4.75 (m, 3H), 3.94 (q, J=7.0 Hz, 2H), 3.07 (m, 5H), 2.77 (d, J=7.6 Hz, 1H), 1.27 (m, 1H), 0.94 (m, 3H), 0.88 (t, J=7.4 Hz, 6H).

Workup

  1. customThe organic layer was separated
  2. washwashed with water
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated in vacuo
  5. customto yield the crude product
  6. customPurification by preparative LCMS (PE SCIEX, C18, acetonitrile—water with 0.035% trifluoroacetic acid)

Sources & evidence

ORD record
ord-588f589c33354149af7ccc6075e7671d
Source dataset
uspto-grants-2008_07
Patent number
US07396936B1

Reaction notes

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