Sodium borohydride → 4-(4'-methylbiphenyl-2-carboxamido)-N-methyl-N-[2-(6-methoxycarbonylhexyloxy)phenyl]benzamide

HRID 323168

반응식

HRID 323168 반응식
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:9]([C:14]([NH:16][C:17]3[CH:43]=[CH:42][C:20]([C:21]([N:23]([CH3:41])[C:24]4[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=4[O:30][CH2:31][CH2:32][CH2:33][CH2:34][CH:35]=[CH:36][C:37]([O:39][CH3:40])=[O:38])=[O:22])=[CH:19][CH:18]=3)=[O:15])=[CH:10][CH:11]=[CH:12][CH:13]=2)=[CH:4][CH:3]=1.[BH4-].[Na+]>CO.O1CCCC1.O.O.O.O.O.O.[Ni](Cl)Cl>[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:9]([C:14]([NH:16][C:17]3[CH:43]=[CH:42][C:20]([C:21]([N:23]([CH3:41])[C:24]4[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=4[O:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][C:37]([O:39][CH3:40])=[O:38])=[O:22])=[CH:19][CH:18]=3)=[O:15])=[CH:10][CH:11]=[CH:12][CH:13]=2)=[CH:4][CH:3]=1

참가 물질

6

반응 조건

온도
0 °C

실험 절차

A solution of 4-(4′-methylbiphenyl-2-carboxamido)-N-methyl-N-[2-(6-methoxycarbonyl-5-hexenyloxy)phenyl]benzamide (360 mg) and nickel chloride hexahydrate (594 mg) in methanol (15 ml) and tetrahydrofuran (15 ml) was treated at 0° C. with sodium borohydride (283 mg) and stirred at 0° C. for 4 hours. The reaction mixture was diluted with tetrahydrofuran and filtered through a bed of Celite and then concentrated. The residue was diluted with ethyl acetate and washed with water and brine. The organic layer was dried over magnesium sulfate, concentrated to give 4-(4′-methylbiphenyl-2-carboxamido)-N-methyl-N-[2-(6-methoxycarbonylhexyloxy)phenyl]benzamide (340 mg).

후처리

  1. filtrationfiltered through a bed of Celite
  2. concentrationconcentrated
  3. additionThe residue was diluted with ethyl acetate
  4. washwashed with water and brine
  5. dry with materialThe organic layer was dried over magnesium sulfate
  6. concentrationconcentrated

출처 및 근거

ORD 기록
ord-b3afac3601d14e4897952eb973a83c22
출처 데이터셋
uspto-grants-2001_04
특허 번호
US06211242B1

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