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

HRID 1177839노트

반응식

HRID 1177839 반응식
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

참가 물질

5

반응물 2

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

생성물 1

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

시약·촉매·용매 2

HCID 23938Palladium촉매HCID 887Methanol용매

반응 조건

온도
75 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-b52a3cc0575645359c5d5e03318d41a0
출처 데이터셋
uspto-grants-2010_11
특허 번호
US07842696B2

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