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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 14045
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HRID 14045 반응식
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
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참가 물질

4

반응물 1

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

생성물 1

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

시약·촉매·용매 2

HCID 23938Palladium촉매HCID 176Acetic Acid용매

실험 절차

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; gradient of dichloromethane/methanol/ammonium hydroxide 97/3/0.05 to 93/7/0.05) to give the title compound: NMR (300 MHz, CD3OD): δ 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.

후처리

  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; gradient of dichloromethane/methanol/ammonium hydroxide 97/3/0.05 to 93/7/0.05)

출처 및 근거

ORD 기록
ord-13bb5b517c8040dab3c2d6b0aaa4e021
출처 데이터셋
uspto-grants-2010_06
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07727997B2

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