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Cesium carbonate → Tert-butyl 4-(3-((R)-3-(((S)-3-(tert-butoxy)-3-oxo-1-(4-(2-(tosyloxy)ethoxy)phenyl)propyl)carbamoyl)piperidin-1-YL)-3-oxopropyl)piperidine-1-carboxylate

HRID 526370
ノート
印刷プレビュー

反応式

HRID 526370 の反応式
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([CH2:14][CH2:15][C:16]([N:18]2[CH2:23][CH2:22][CH2:21][C@@H:20]([C:24](=[O:42])[NH:25][C@H:26]([C:35]3[CH:40]=[CH:39][C:38]([OH:41])=[CH:37][CH:36]=3)[CH2:27][C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29])[CH2:19]2)=[O:17])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(=O)([O-])[O-].[Cs+].[Cs+].[C:49]1([CH3:72])[CH:54]=[CH:53][C:52]([S:55]([O:58][CH2:59][CH2:60]OS(C2C=CC(C)=CC=2)(=O)=O)(=[O:57])=[O:56])=[CH:51][CH:50]=1>CN(C)C=O>[C:31]([O:30][C:28](=[O:29])[CH2:27][C@H:26]([NH:25][C:24]([C@@H:20]1[CH2:21][CH2:22][CH2:23][N:18]([C:16](=[O:17])[CH2:15][CH2:14][CH:11]2[CH2:10][CH2:9][N:8]([C:6]([O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[O:7])[CH2:13][CH2:12]2)[CH2:19]1)=[O:42])[C:35]1[CH:40]=[CH:39][C:38]([O:41][CH2:60][CH2:59][O:58][S:55]([C:52]2[CH:53]=[CH:54][C:49]([CH3:72])=[CH:50][CH:51]=2)(=[O:57])=[O:56])=[CH:37][CH:36]=1)([CH3:32])([CH3:33])[CH3:34]
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 10796Cesium carbonateHCID 228289Ethylene glycol ditosylateHCID 712589314-(3-{(R)-3-[(S)-2-tert-butoxycarbonyl-1-(4-hydroxy-phenyl)-ethylcarbamoyl]-piperidin-1-yl}-3-oxo-propyl)-piperidine-1-carboxylic acid tert-butyl ester

生成物 1

HCID 89407760Tert-butyl 4-(3-((R)-3-(((S)-3-(tert-butoxy)-3-oxo-1-(4-(2-(tosyloxy)ethoxy)phenyl)propyl)carbamoyl)piperidin-1-YL)-3-oxopropyl)piperidine-1-carboxylate収率 63%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

270.0 mg (0.46 mmol) 4-(3-{(R)-3-[(S)-2-tert-butoxycarbonyl-1-(4-hydroxy-phenyl)-ethylcarbamoyl]-piperidin-1-yl}-3-oxo-propyl)-piperidine-1-carboxylic acid tert-butyl ester were dissolved in 17.7 ml N,N-dimethylformamide. 449 mg (1.38 mmol) cesium carbonate and 255.3 mg (0.69 mmol) ethylene glycol bis-p-toluenesulfonate were added. The mixture was stirred at room temperature for 20 hours and concentrated. The remainder was taken up with saturated ammonium chloride solution and ethyl acetate. The aqueous phase was extracted with 3×20 ml ethyl acetate. The extracts were dried over sodium sulfate and concentrated. Chromatography over 10 g silica gel (dichloromethane/ethanol 100/0-90/10) gave 227 mg (63%) tert-butyl 4-{3-[(3R)-3-({(1S)-3-tert-butoxy-1-[4-(2-{[(4-methylphenyl)sulfonyl]oxy}ethoxy)phenyl]-3-oxopropyl}carbamoyl)piperidin-1-yl]-3-oxopropyl}piperidine-1-carboxylate which were purified by HPLC:

後処理

  1. concentrationconcentrated
  2. extractionThe aqueous phase was extracted with 3×20 ml ethyl acetate
  3. dry with materialThe extracts were dried over sodium sulfate
  4. concentrationconcentrated

出典と根拠

ORDレコード
ord-11e8e2ec4de6481b9aebbf7155573a1b
出典データセット
uspto-grants-2016_05
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09345793B2

反応ノート

読み込み中…

このページの内容参加物実験手順後処理出典と根拠反応ノート