Trifluoroacetic anhydride → HCID 136167040, compound

HRID 1617983Notes

Reaction equation

HRID 1617983 reaction equation
FC(F)(F)C(OC(=O)C(F)(F)F)=[O:4].[C:14]([CH:17]1[CH2:22][CH2:21][N:20]([C:23]2[CH:28]=[CH:27][C:26]([C@H:29]([C:42]3[CH:47]=[CH:46][CH:45]=[CH:44][C:43]=3[CH3:48])[CH2:30]/[C:31](/[C:34]3[CH:39]=[CH:38][N+:37]([O-])=[C:36]([CH3:41])[CH:35]=3)=[N:32]\[OH:33])=[CH:25][CH:24]=2)[CH2:19][CH2:18]1)([OH:16])=[O:15].[OH-].[Na+]>ClCCl>[OH:33]/[N:32]=[C:31](/[C:34]1[CH:39]=[CH:38][N:37]=[C:36]([CH2:41][OH:4])[CH:35]=1)\[CH2:30][C@H:29]([C:26]1[CH:27]=[CH:28][C:23]([N:20]2[CH2:21][CH2:22][CH:17]([C:14]([OH:16])=[O:15])[CH2:18][CH2:19]2)=[CH:24][CH:25]=1)[C:42]1[CH:47]=[CH:46][CH:45]=[CH:44][C:43]=1[CH3:48]

Participants

5

Reactant 3

HCID 9845Trifluoroacetic anhydride2×HCID 14798Sodium HydroxideHCID 178424250HCID 178424250, compound

Product 1

HCID 136167040HCID 136167040, compoundYield 14%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Trifluoroacetic anhydride (421 mg, 2.01 mmol) was added at 0° C. to a suspension of (R,E)-4-(3-(4-(4-carboxypiperidin-1-yl)phenyl)-1-(hydroxyimino)-3-o-tolylpropyl)-2-methyl-pyridine 1-oxide (95 mg, 201 μmol) in dichloromethane (3 mL) to give a white suspension, then after 1 h another portion of trifluoroacetic anhydride (421 mg, 2.01 mmol) was added. The reaction mixture was allowed to reach room temperature over 1 h, then treated with 1 M aq. sodium hydroxide solution and stirred for another 90 min. After extraction with dichloromethane, the organic layer was washed with brine, dried over sodium sulfate, filtered, and evaporated. The residue was purified by preparative HPLC to produce the title compound (13 mg, 14%). Light yellow oil, MS (ESI+): m/z=474.4 ([M+H]+).

Workup

  1. customto give a white suspension
  2. extractionAfter extraction with dichloromethane
  3. washthe organic layer was washed with brine
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. customevaporated
  7. customThe residue was purified by preparative HPLC

Sources & evidence

ORD record
ord-3d7a8a285b9c451eb61eed43b735093c
Source dataset
uspto-grants-2014_07
Patent number
US08765730B2

Reaction notes

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