2-Amino-4-(benzyloxy)benzamide → HCID 66610642、化合物

HRID 625774ノート

反応式

HRID 625774 の反応式
[NH2:1][C:2]1[CH:10]=[C:9]([O:11][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH:8]=[CH:7][C:3]=1[C:4]([NH2:6])=[O:5].[F:19][C:20]1[CH:25]=[CH:24][C:23]([CH:26]2[O:30]C(=O)[O:28][C:27]2=O)=[CH:22][CH:21]=1>C1COCC1>[CH2:12]([O:11][C:9]1[CH:8]=[CH:7][C:3]([C:4]([NH2:6])=[O:5])=[C:2]([NH:1][C:27](=[O:28])[CH:26]([C:23]2[CH:24]=[CH:25][C:20]([F:19])=[CH:21][CH:22]=2)[OH:30])[CH:10]=1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

参加物

4

反応物 2

HCID 231302772-Amino-4-(benzyloxy)benzamideHCID 866490505-(4-Fluorophenyl)-1,3-dioxolane-2,4-dione

生成物 1

HCID 66610642HCID 66610642、化合物収率 64%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
63 °C

実験手順

To a solution of 2-amino-4-(benzyloxy)benzamide (4.0 g, 16.5 mmol) in THF (60 mL) was added a solution of 5-(4-fluorophenyl)-1,3-dioxolane-2,4-dione (3.65 g, 18.6 mmol) from Example 16 in THF (20 mL) portionwise at rt. After heating to 63° C. for 18 h, the solution was cooled and concentrated. After addition of H2O, the solution was extracted twice with DCM. The combined organic phases were washed with brine and dried over sodium sulfate. Chromatography on silica gel eluting with 10 to 80% EtOAc/DCM afforded 4-(benzyloxy)-2-(2-(4-fluorophenyl)-2-hydroxyacetamido)benzamide as a foamy solid (4.1 g, 64%). 1H NMR (300 MHz, DMSO-d6) δ ppm 5.06 (m, 1H), 5.12 (s, 2H) 6.68-6.74 (m, 1H) 7.14-7.20 (m, 2H) 7.32-7.51 (m, 6H) 7.77 (d, J=8.85 Hz, 1H) 8.05 (br. s., 1H) 8.30 (d, J=2.64 Hz, 1H) 12.73 (s, 1H). LC-MS (ESI) m/z 392 (M−2).

後処理

  1. temperaturethe solution was cooled
  2. concentrationconcentrated
  3. additionAfter addition of H2O
  4. extractionthe solution was extracted twice with DCM
  5. washThe combined organic phases were washed with brine
  6. dry with materialdried over sodium sulfate

出典と根拠

ORDレコード
ord-95273d2098394866812ae15a834514ec
出典データセット
uspto-grants-2016_04
特許番号
US09308207B2

反応ノート

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