Water → tert-butyl [(3S)-3-hydroxy-4-oxo-4-((5-(tritylamino)-1-[2-(trityloxy)ethyl]-1H-pyrazol-4-yl)amino)butyl]carbamate

HRID 459628ノート

反応式

HRID 459628 の反応式
[OH:1][C@H:2]([C:13]([NH:15][C:16]1[CH:17]=[N:18][N:19]([CH2:41][CH2:42][OH:43])[C:20]=1[NH:21][C:22]([C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1)([C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)=[O:14])[CH2:3][CH2:4][NH:5][C:6](=[O:12])[O:7][C:8]([CH3:11])([CH3:10])[CH3:9].[C:44](Cl)([C:57]1[CH:62]=[CH:61][CH:60]=[CH:59][CH:58]=1)([C:51]1[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=1)[C:45]1[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=1.C(N(CC)CC)C.O>CN(C)C=O.CN(C)C1C=CN=CC=1>[OH:1][C@H:2]([C:13](=[O:14])[NH:15][C:16]1[CH:17]=[N:18][N:19]([CH2:41][CH2:42][O:43][C:44]([C:45]2[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=2)([C:57]2[CH:58]=[CH:59][CH:60]=[CH:61][CH:62]=2)[C:51]2[CH:52]=[CH:53][CH:54]=[CH:55][CH:56]=2)[C:20]=1[NH:21][C:22]([C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1)([C:29]1[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=1)[C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1)[CH2:3][CH2:4][NH:5][C:6](=[O:12])[O:7][C:8]([CH3:9])([CH3:10])[CH3:11]

参加物

7

反応物 4

HCID 962WaterHCID 6456Trityl chlorideHCID 8471TriethylamineHCID 69651947tert-butyl ((3S)-3-hydroxy-4-{[1-(2-hydroxyethyl)-5-(tritylamino)-1H-pyrazol-4-yl]amino}-4-oxobutyl)carbamate

生成物 1

HCID 69651992tert-butyl [(3S)-3-hydroxy-4-oxo-4-((5-(tritylamino)-1-[2-(trityloxy)ethyl]-1H-pyrazol-4-yl)amino)butyl]carbamate収率 42.4%

試薬・触媒・溶媒 2

HCID 142844-(Dimethylamino)pyridine触媒HCID 6228Dimethylformamide溶媒

反応条件

温度
60 °C

実験手順

To a stirred solution of tert-butyl ((3S)-3-hydroxy-4-{[1-(2-hydroxyethyl)-5-(tritylamino)-1H-pyrazol-4-yl]amino}-4-oxobutyl)carbamate (2.5 g) in N,N-dimethylformamide (25 ml) were added trityl chloride (1.25 g), triethylamine (1.78 ml) and 4-dimethylaminopyridine (52.1 mg), and the mixture was stirred for 1 hour. The reaction mixture was warmed up to 60° C. and stirred at the same temperature for 2 days. Water was added to the mixture, and the whole mixture was extracted with ethyl acetate. The extract was washed with water and brine and dried over anhydrous magnesium sulfate. Concentration under reduced pressure gave an oil, which was purified by column chromatography on silica gel (methylene chloride:ethyl acetate=5:1) to give tert-butyl [(3S)-3-hydroxy-4-oxo-4-({5-(tritylamino)-1-[2-(trityloxy)ethyl]-1H-pyrazol-4-yl}amino)butyl]carbamate (1.5 g).

後処理

  1. stirringstirred at the same temperature for 2 days
  2. extractionthe whole mixture was extracted with ethyl acetate
  3. washThe extract was washed with water and brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationConcentration under reduced pressure
  6. customgave an oil, which
  7. customwas purified by column chromatography on silica gel (methylene chloride:ethyl acetate=5:1)

出典と根拠

ORDレコード
ord-18b1f41a55f9437aa2958e3999ff71ab
出典データセット
uspto-grants-2007_03
特許番号
US07192943B2

反応ノート

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