Triethylamine → N1-{(1S,2R)-1-(3,5-difluorobenzyl)-3-[(2-furylmethyl)amino]-2-hydroxypropyl)-5-methyl-N3,N3-dipropylisophthalamide

HRID 14012

反応式

HRID 14012 の反応式
[C:1]([OH:4])(=O)[CH3:2].[NH2:5][CH2:6][C@@H:7]([OH:37])[C@@H:8]([NH:18][C:19](=[O:36])[C:20]1[CH:34]=[C:33]([CH3:35])[CH:32]=[C:22]([C:23]([N:25]([CH2:29][CH2:30][CH3:31])[CH2:26][CH2:27][CH3:28])=[O:24])[CH:21]=1)[CH2:9][C:10]1[CH:15]=[C:14]([F:16])[CH:13]=[C:12]([F:17])[CH:11]=1.O1C=[CH:41][C:40](C=O)=[CH:39]1.C(N(CC)CC)C>C(O)C.[Pd]>[F:16][C:14]1[CH:15]=[C:10]([CH:11]=[C:12]([F:17])[CH:13]=1)[CH2:9][C@H:8]([NH:18][C:19](=[O:36])[C:20]1[CH:34]=[C:33]([CH3:35])[CH:32]=[C:22]([C:23]([N:25]([CH2:26][CH2:27][CH3:28])[CH2:29][CH2:30][CH3:31])=[O:24])[CH:21]=1)[C@H:7]([OH:37])[CH2:6][NH:5][CH2:41][C:40]1[O:4][CH:1]=[CH:2][CH:39]=1

参加物

6

反応物 3

HCID 8471TriethylamineHCID 103513-FuraldehydeHCID 68609581N1-[(1S,2R)-3-amino-1-(3,5-difluorobenzyl)-2-hydroxypropyl]-5-methyl-N3,N3-dipropylisophthalamide Acetic Acid Salt

生成物 1

HCID 10280514N1-{(1S,2R)-1-(3,5-difluorobenzyl)-3-[(2-furylmethyl)amino]-2-hydroxypropyl)-5-methyl-N3,N3-dipropylisophthalamide

試薬・触媒・溶媒 2

HCID 23938Palladium触媒HCID 702Ethanol溶媒

反応条件

温度
22.5 °C

実験手順

N1-[(1S,2R)-3-amino-1-(3,5-difluorobenzyl)-2-hydroxypropyl]-5-methyl-N3,N3-dipropylisophthalamide acetic acid salt (XVI, EXAMPLE 168, 76 mg, 0.146 mmol) is dissolved in absolute ethanol (2 mL). 3-Furaldehyde (20 microL, 0.231 mmol) and triethylamine (30 microL, 0.215 mmol) are added via syringe, with stirring at 20-25 degrees C. After 10 minutes, palladium on carbon 122 mg, 5 weight %) is added and the mixture placed under a hydrogen atmosphere (50 psi) and shaken for 20 minutes. The resulting mixture is then filtered through diatomaceous earth, with ethanol washings. The filtrate is purified by flash chromatography (2-10% methanol/methylene chloride) to give purified title compound, MS (MH+)=542.2.

後処理

  1. stirringshaken for 20 minutes
  2. filtrationThe resulting mixture is then filtered through diatomaceous earth, with ethanol washings
  3. customThe filtrate is purified by flash chromatography (2-10% methanol/methylene chloride)
  4. customto give
  5. custompurified title compound, MS (MH+)=542.2

出典と根拠

ORDレコード
ord-afb7b8cbd925479a9280ad7e80cb37de
出典データセット
uspto-grants-2010_06
特許番号
US07727997B2

関連ノート

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