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Cesium carbonate → Di-tert-butyl (4S)-N-(tert-butoxycarbonyl)-4-{4-[3-(tosyloxy)propoxy]benzyl}-L-glutamate

HRID 591258
ノート
印刷プレビュー

反応式

HRID 591258 の反応式
[C:1]([O:5][C:6]([NH:8][C@H:9]([C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])[CH2:10][C@H:11]([CH2:19][C:20]1[CH:25]=[CH:24][C:23]([OH:26])=[CH:22][CH:21]=1)[C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])=[O:7])([CH3:4])([CH3:3])[CH3:2].C(=O)([O-])[O-].[Cs+].[Cs+].[C:40]1([CH3:64])[CH:45]=[CH:44][C:43]([S:46]([O:49][CH2:50][CH2:51][CH2:52]OS(C2C=CC(C)=CC=2)(=O)=O)(=[O:48])=[O:47])=[CH:42][CH:41]=1>CN(C)C=O>[C:1]([O:5][C:6]([NH:8][C@H:9]([C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])[CH2:10][C@H:11]([CH2:19][C:20]1[CH:25]=[CH:24][C:23]([O:26][CH2:52][CH2:51][CH2:50][O:49][S:46]([C:43]2[CH:42]=[CH:41][C:40]([CH3:64])=[CH:45][CH:44]=2)(=[O:47])=[O:48])=[CH:22][CH:21]=1)[C:12]([O:14][C:15]([CH3:16])([CH3:18])[CH3:17])=[O:13])=[O:7])([CH3:2])([CH3:3])[CH3:4]
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 2303703-(4-Methylphenyl)sulfonyloxypropyl 4-methylbenzenesulfonateHCID 70957078di-tert-butyl (4S)-N-(tert-butoxycarbonyl)-4-(4-hydroxybenzyl)-L-glutamate

生成物 1

HCID 70674889Di-tert-butyl (4S)-N-(tert-butoxycarbonyl)-4-{4-[3-(tosyloxy)propoxy]benzyl}-L-glutamate

試薬・触媒・溶媒 1

HCID 6228
Dimethylformamide
溶媒

実験手順

To 100 mg (0.22 mmol) of di-tert-butyl (4S)—N-(tert-butoxycarbonyl)-4-(4-hydroxy-benzyl)-L-glutamate (Example 1b) in 10 mL N,N-dimethylformamide were added 210 mg (0.64 mmol) of cesium carbonate and 413 mg (1.07 mmol) of 1,3-propanediol di-p-toluenesulfonate (Aldrich) and the resulting suspension was stirred overnight at room temperature. The reaction mixture was then filtered, the solvent evaporated and the residue was taken up in dichloromethane and 1 M hydrochloric acid. The organic phase was separated off, washed with water until neutral, dried over sodium sulfate and filtered, and the filtrate was concentrated in vacuo. The crude product obtained in this manner was chromatographed on silica gel using a hexane/ethyl acetate gradient, and the appropriate fractions were combined and concentrated.

後処理

  1. filtrationThe reaction mixture was then filtered
  2. customthe solvent evaporated
  3. customThe organic phase was separated off
  4. washwashed with water until neutral,
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationthe filtrate was concentrated in vacuo

出典と根拠

ORDレコード
ord-bd60d660f8cb4eb9b2f431b4a464a96c
出典データセット
uspto-grants-2016_01
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09238631B2

反応ノート

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