Triethylamine → 2-(4'-fluorobiphenyl-4-yl)-N-hydroxy-2-phenylacetamide

HRID 509180

Reaction equation

HRID 509180 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([CH:14]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[C:15](O)=[O:16])=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.F[P-](F)(F)(F)(F)F.[N:31]1([O:40][P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1.Cl.NO.C(N(CC)CC)C>N1C=CC=CC=1>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([CH:14]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[C:15]([NH:31][OH:40])=[O:16])=[CH:10][CH:9]=2)=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 443297Hydroxyamine hydrochlorideHCID 577796832-(4'-Fluorobiphenyl-4-yl)-2-phenylacetic acid

Product 1

HCID 577796132-(4'-fluorobiphenyl-4-yl)-N-hydroxy-2-phenylacetamideYield 48%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of 13 (40 mg, 0.14 mmol), BOP (58 mg, 0.13 mmol), and hydroxylamine hydrochloride (9 mg, 0.13 mmol) in pyridine (5 mL) was added triethylamine (0.055 mL, 0.39 mmol) and the reaction mixture was stirred at room temperature for 2 h. The solvents were removed under vacuum and the crude was dissolved in ethyl acetate. The organic layer was washed with water, dried over Na2SO4, filtered and concentrated. The residue was purified via HPLC (Gilson) reverse-phase column with a gradient of methanol (20-75%) in water to afford compound 14 as a white solid (20 mg, 48%). 1H NMR (CD3OD-d4) δ (ppm): 7.62-7.57 (m, 2H), 7.53 (d, J=8.2 Hz, 2H), 7.40-7.22 (m, 7H), 7.14 (t, J=8.8 Hz, 2H), 4.82 (s, 1H). LRMS (ESI): (calc.) 321.1 (found) 320.4 (MH)−.

Workup

  1. customThe solvents were removed under vacuum
  2. dissolutionthe crude was dissolved in ethyl acetate
  3. washThe organic layer was washed with water
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified via HPLC (Gilson) reverse-phase column with a gradient of methanol (20-75%) in water

Sources & evidence

ORD record
ord-9f596383458f40dab57e980dd79d8e61
Source dataset
uspto-grants-2015_08
Patent number
US09096565B2

Linked notes

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