Trifluoroacetic acid → HCID 25000227, compound

HRID 747654Notes

Reaction equation

HRID 747654 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]3C=N[CH:51]=[CH:52][CH:53]=3)=[CH:41][CH:40]=2)[C:37]([C:55](=[O:57])[NH2:56])=[C:36]([CH2:58][CH3:59])[NH:35][C:34]=1[CH2:60][CH2:61][C:62]1[CH:67]=[CH:66][C:65]([F:68])=[CH:64][CH:63]=1)=[O:32])[CH3:29].FC(F)(F)C(O)=[O:72]>C(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[O:72][CH:51]=[CH:52][CH:53]=3)=[CH:41][CH:40]=2)=[C:37]([C:55](=[O:57])[NH2:56])[C:36]([CH2:58][CH3:59])=[N:35][C:34]=1[CH2:60][CH2:61][C:62]1[CH:67]=[CH:66][C:65]([F:68])=[CH:64][CH:63]=1)[CH3:29]

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 180504Ceric ammonium nitrateHCID 59749720HCID 59749720, compound

Product 1

HCID 25000227HCID 25000227, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

An aqueous solution of CAN (1 M, 1 mL) was added to 2 mL of DCM solution of compound 16 (˜0.25 mmol) and trifluoroacetic acid (0.1 mL). The resulting mixture was vigorously stirred for 20 min at r.t. The organic layer was separated, washed with water, dried over MgSO4, 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 in 18.5 mg yield. LC/MS (gradient 40-99%, 5 min.) RT=3.215. Calculated mass=243.2. Mass observed=243.7. 1H NMR (500 MHz, CDCl3): δ 0.88 (t, 3H), 1.36 (t, 3H), 2.98 (bq, 2H), 3.07 (bq, 2H), 3.15 (bq, 2H), 3.94 (q, 2H), 4.65 (d, 2H), 5.61 (bs, 1H), 6.32 (m, 1H), 6.36 (m, 1H), 6.61 (bt, 1H), 6.96 (t, 2H), 7.18 (t, 2H), 7.39 (s, 1H), 7.40 (d, 2H), 7.81 (d, 2H).

Workup

  1. customThe organic layer was separated
  2. washwashed with water
  3. dry with materialdried over MgSO4
  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-aa280f06c0c441c2bae5b018b1bed4ff
Source dataset
uspto-grants-2008_07
Patent number
US07396936B1

Reaction notes

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