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Cesium carbonate → (RS)-tert-butoxycarbonylamino-[4-(2-methoxy-ethoxy)-phenyl]-acetic acid methyl ester

HRID 1911518
ノート
印刷プレビュー

反応式

HRID 1911518 の反応式
[CH3:1][O:2][C:3](=[O:20])[CH:4]([NH:12][C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[C:5]1[CH:10]=[CH:9][C:8]([OH:11])=[CH:7][CH:6]=1.[CH3:21][O:22][CH2:23][CH2:24]Br.C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C.[I-].C([N+](CCCC)(CCCC)CCCC)CCC>[CH3:1][O:2][C:3](=[O:20])[CH:4]([NH:12][C:13]([O:15][C:16]([CH3:17])([CH3:19])[CH3:18])=[O:14])[C:5]1[CH:6]=[CH:7][C:8]([O:11][CH2:24][CH2:23][O:22][CH3:21])=[CH:9][CH:10]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 3

HCID 10796Cesium carbonateHCID 809722-Bromoethyl methyl etherHCID 11644846Methyl 2-(Boc-amino)-2-(4-hydroxyphenyl)acetate

生成物 1

HCID 57608579(RS)-tert-butoxycarbonylamino-[4-(2-methoxy-ethoxy)-phenyl]-acetic acid methyl ester収率 72%

試薬・触媒・溶媒 2

HCID 67553Tetrabutylammonium Iodide触媒
HCID 6228
Dimethylformamide
溶媒

実験手順

A solution of (RS)-tert-butoxycarbonylamino-(4-hydroxy-phenyl)-acetic acid methyl ester (500 mg, CAS 143323-49-3) in DMF (4 ml) was treated under an argon atmosphere with 2-bromoethyl methyl ether (0.34 ml), cesium carbonate (695 mg) and tetrabutylammonium iodide (66 mg) and stirred at r.t. overnight. Then it was quenched with H2O and extracted with EtOAc. The organics were washed with water, dried over MgSO4, filtrated and concentrated. The crude product was purified by column chromatography (silica gel; gradient: cyclohexane ->cyclohexane/EtOAc 4:1) to give (RS)-tert-butoxycarbonylamino-[4-(2-methoxy-ethoxy)-phenyl]-acetic acid methyl ester (434 mg, 72%) as viscous colorless oil.

後処理

  1. customThen it was quenched with H2O
  2. extractionextracted with EtOAc
  3. washThe organics were washed with water
  4. dry with materialdried over MgSO4
  5. filtrationfiltrated
  6. concentrationconcentrated
  7. customThe crude product was purified by column chromatography (silica gel; gradient: cyclohexane ->cyclohexane/EtOAc 4:1)

出典と根拠

ORDレコード
ord-5b67aa41fd194e01ad71c4d7a8e0fb9e
出典データセット
uspto-grants-2013_12
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08604061B2

反応ノート

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