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

HRID 323168
ノート
印刷プレビュー

反応式

HRID 323168 の反応式
[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
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

6

反応物 2

HCID 4311764Sodium borohydrideHCID 700705814-(4'-methylbiphenyl-2-carboxamido)-N-methyl-N-[2-(6-methoxycarbonyl-5-hexenyloxy)phenyl]benzamide

生成物 1

HCID 220106784-(4'-methylbiphenyl-2-carboxamido)-N-methyl-N-[2-(6-methoxycarbonylhexyloxy)phenyl]benzamide収率 94.1%

試薬・触媒・溶媒 3

HCID 11791229Dichloronickel;hexahydrate触媒
HCID 887
Methanol
溶媒
HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
0 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-b3afac3601d14e4897952eb973a83c22
出典データセット
uspto-grants-2001_04
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US06211242B1

反応ノート

読み込み中…

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