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N1-{(1S,2R)-1-[4-(benzyloxy)benzyl]-2-hydroxy-3-[(3-methoxybenzyl)amino]propyl}-N3-[4-(benzyloxy)butyl]-5-methyl-N3-propylisophthalamide → N1-(4-hydroxybutyl)-N3-{(1S)-2-hydroxy-1-(4-hydroxybenzyl)-3-[(3-methoxybenzyl)amino]propyl}-5-methyl-N1-propylisophthalamide

HRID 1783259
ノート
印刷プレビュー

反応式

HRID 1783259 の反応式
C([O:8][C:9]1[CH:57]=[CH:56][C:12]([CH2:13][C@H:14]([NH:28][C:29](=[O:55])[C:30]2[CH:53]=[C:52]([CH3:54])[CH:51]=[C:32]([C:33]([N:35]([CH2:39][CH2:40][CH2:41][CH2:42][O:43]CC3C=CC=CC=3)[CH2:36][CH2:37][CH3:38])=[O:34])[CH:31]=2)[C@H:15]([OH:27])[CH2:16][NH:17][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[C:21]([O:25][CH3:26])[CH:20]=2)=[CH:11][CH:10]=1)C1C=CC=CC=1>[Pd].C(O)(=O)C>[OH:43][CH2:42][CH2:41][CH2:40][CH2:39][N:35]([CH2:36][CH2:37][CH3:38])[C:33](=[O:34])[C:32]1[CH:51]=[C:52]([CH3:54])[CH:53]=[C:30]([C:29]([NH:28][C@@H:14]([CH2:13][C:12]2[CH:56]=[CH:57][C:9]([OH:8])=[CH:10][CH:11]=2)[CH:15]([OH:27])[CH2:16][NH:17][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[C:21]([O:25][CH3:26])[CH:20]=2)=[O:55])[CH:31]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

4

反応物 1

HCID 68609530N1-{(1S,2R)-1-[4-(benzyloxy)benzyl]-2-hydroxy-3-[(3-methoxybenzyl)amino]propyl}-N3-[4-(benzyloxy)butyl]-5-methyl-N3-propylisophthalamide

生成物 1

HCID 68608790N1-(4-hydroxybutyl)-N3-{(1S)-2-hydroxy-1-(4-hydroxybenzyl)-3-[(3-methoxybenzyl)amino]propyl}-5-methyl-N1-propylisophthalamide

試薬・触媒・溶媒 2

HCID 23938Palladium触媒HCID 176Acetic Acid溶媒

実験手順

A mixture of N1-{(1S,2R)-1-[4-(benzyloxy)benzyl]-2-hydroxy-3-[(3-methoxybenzyl)amino]propyl}-N3-[4-(benzyloxy)butyl]-5-methyl-N3-propylisophthalamide (X, 100 mg, 0.130 mmol) and palladium on carbon (10%, 100 mg) in absolute glacial acetic acid (5 mL) is shaken under an atmosphere of hydrogen at 35 psi for 5 hours. The resulting mixture is filtered through diatomaceous earth and washed with methanol. The combined filtrates are concentrated under reduced pressure. The concentrate is purified by flash column chromatography (silica; gradent of dichloromethane/methanol/ammonium hydroxide 97/3/0.05 to 93/7/0.05) to give the title compound: NMR (300 MHz, CD3OD): □ 7.55-6.64, 4.19, 3.99-3.72, 3.63-3.36, 3.21-3.09, 2.79-2.69, 2.39, 1.90-1.40, 1.29 and 1.02-0.6; ESI-MS (m/z) [M+H]+=592.

後処理

  1. filtrationThe resulting mixture is filtered through diatomaceous earth
  2. washwashed with methanol
  3. concentrationThe combined filtrates are concentrated under reduced pressure
  4. customThe concentrate is purified by flash column chromatography (silica; gradent of dichloromethane/methanol/ammonium hydroxide 97/3/0.05 to 93/7/0.05)

出典と根拠

ORDレコード
ord-72bcc2ed2cd440258279a92022e1e9cc
出典データセット
uspto-grants-2009_03
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07498436B2

反応ノート

読み込み中…

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