Trifluoroacetic acid → Trifluoroacetate

HRID 1186045Notes

Reaction equation

HRID 1186045 reaction equation
C(O[CH:4]([O:21]CC)[CH2:5][CH:6]1[CH2:20][O:19][C:10]2=[CH:11][C:12]3[CH2:13][NH:14][C:15](=[NH:18])[C:16]=3[CH:17]=[C:9]2[O:8][CH2:7]1)C.Br[CH2:25][C:26]([C:28]1[CH:33]=[C:32]([C:34]([CH3:37])([CH3:36])[CH3:35])[C:31]([OH:38])=[C:30]([C:39]([CH3:42])([CH3:41])[CH3:40])[CH:29]=1)=[O:27].[C:43]([OH:49])([C:45]([F:48])([F:47])[F:46])=[O:44]>CN(C=O)C.C(Cl)Cl>[C:34]([C:32]1[CH:33]=[C:28]([C:26](=[O:27])[CH2:25][N:14]2[CH2:13][C:12]3[CH:11]=[C:10]4[O:19][CH2:20][CH:6]([CH2:5][CH:4]=[O:21])[CH2:7][O:8][C:9]4=[CH:17][C:16]=3[C:15]2=[NH:18])[CH:29]=[C:30]([C:39]([CH3:42])([CH3:41])[CH3:40])[C:31]=1[OH:38])([CH3:37])([CH3:35])[CH3:36].[F:46][C:45]([F:48])([F:47])[C:43]([O-:49])=[O:44]

Participants

7

Reactant 3

HCID 6422Trifluoroacetic acidHCID 6161612-Bromo-1-[3,5-di(tert-butyl)-4-hydroxyphenyl]ethan-1-oneHCID 178467751HCID 178467751, compound

Product 2

HCID 84468TrifluoroacetateHCID 58245687HCID 58245687, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

The residue prepared in STEP B above (850 mg, 2.65 mmol) in DMF (10 mL) was combined with 2-bromo-1-[3,5-di(tert-butyl)-4-hydroxyphenyl]ethan-1-one (1.04 g, 3.18 mmol) and stirred at room temperature for 18 h. The resulting mixture was evaporated in vacuo to yield an oil, which was treated with 50% TFA in DCM at 0° C. The solvent was then evaporated, and the residue purified via reverse phase HPLC to yield 2-(8-(2-(3,5-di-tert-butyl-4-hydroxyphenyl)-2-oxoethyl)-7-imino-2,3,4,7,8,9-hexahydro-[1,4]dioxepino[2,3-f]isoindol-3-yl)acetaldehyde as its corresponding trifluoroacetate salt, as a residue. MS MH+=493; 1H NMR (CDCl3): d 8.88 (bs, 1H), 7.83 (s, 2H), 7.66 (s, 1H), 7.05 (s, 1H), 5.85 (bs, 1H), 4.67 (s, 2H), 4.36 (m, 2H), 4.11 (m, 4H), 2.91 (m, 1H), 2.76 (m, 2H), 1.45 (s, 18H).

Workup

  1. customThe resulting mixture was evaporated in vacuo
  2. customto yield an oil, which
  3. customThe solvent was then evaporated
  4. customthe residue purified via reverse phase HPLC

Sources & evidence

ORD record
ord-34b13464eed84d20b1d6a25864b38def
Source dataset
uspto-grants-2014_03
Patent number
US08673890B2

Reaction notes

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