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

HRID 509180

反応式

HRID 509180 の反応式
[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

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 1049Pyridine溶媒

実験手順

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)−.

後処理

  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

出典と根拠

ORDレコード
ord-9f596383458f40dab57e980dd79d8e61
出典データセット
uspto-grants-2015_08
特許番号
US09096565B2

関連ノート

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