Ammonium formate → 4-hydroxy-N-[2-oxo-2-(4-phenylacetyl-piperazin-1-yl)-ethyl]-benzamide

HRID 1177839ノート

反応式

HRID 1177839 の反応式
C([O-])=O.[NH4+].C([O:12][C:13]1[CH:39]=[CH:38][C:16]([C:17]([NH:19][CH2:20][C:21](=[O:37])[N:22]2[CH2:27][CH2:26][N:25]([C:28](=[O:36])[CH2:29][C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)[CH2:24][CH2:23]2)=[O:18])=[CH:15][CH:14]=1)C1C=CC=CC=1>CO.[Pd]>[OH:12][C:13]1[CH:14]=[CH:15][C:16]([C:17]([NH:19][CH2:20][C:21](=[O:37])[N:22]2[CH2:23][CH2:24][N:25]([C:28](=[O:36])[CH2:29][C:30]3[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=3)[CH2:26][CH2:27]2)=[O:18])=[CH:38][CH:39]=1

参加物

5

反応物 2

HCID 2723923Ammonium formateHCID 251659104-benzyloxy-N-[2-oxo-2-(4-phenylacetyl-piperazin-1-yl)-ethyl]-benzamide

生成物 1

HCID 251659094-hydroxy-N-[2-oxo-2-(4-phenylacetyl-piperazin-1-yl)-ethyl]-benzamide収率 70%

試薬・触媒・溶媒 2

HCID 23938Palladium触媒HCID 887Methanol溶媒

反応条件

温度
75 °C

実験手順

Ammonium formate (107 mg, 1.6985 mmoles) was added to a mixture of 4-benzyloxy-N-[2-oxo-2-(4-phenylacetyl-piperazin-1-yl)-ethyl]-benzamide (80 mg, 0.17 mmol) in MeOH (15 mL). Pd/C (30 mg in 3 drops of water) was then added and the resulting mixture was refluxed at 75° C. for three hours. The reaction mixture was then filtered through a bed of celite under reduced pressure. The methanol was removed and EtOAc and water were added. The organic layer was extracted, washed with brine, dried over sodium sulphate and concentrated to afford 4-hydroxy-N-[2-oxo-2-(4-phenylacetyl-piperazin-1-yl)-ethyl]-benzamide in 70% yield. LC-MS purity 94.82%. 1H NMR (DMSO-D6): δ 10 (s, 1H), 8.3 (s, 1H), 7.7 (d, 2H), 7.3 (t, 2H), 7.2 (d, 2H), 6.8 (d, 2H), 4.1 (d, 2H), 3.8 (d, 2H), 3.5 (m, 8H).

後処理

  1. filtrationThe reaction mixture was then filtered through a bed of celite under reduced pressure
  2. customThe methanol was removed
  3. additionEtOAc and water were added
  4. extractionThe organic layer was extracted
  5. washwashed with brine
  6. dry with materialdried over sodium sulphate
  7. concentrationconcentrated

出典と根拠

ORDレコード
ord-b52a3cc0575645359c5d5e03318d41a0
出典データセット
uspto-grants-2010_11
特許番号
US07842696B2

反応ノート

読み込み中…