Cesium carbonate → N-{4-Chloro-2-[(2S)-oxiran-2-ylmethoxy]phenyl}acetamide

HRID 270074

反応式

HRID 270074 の反応式
[O:1]1[CH2:3][C@H:2]1[CH2:4]OS(C1C=CC=C([N+]([O-])=O)C=1)(=O)=O.[Cl:18][C:19]1[CH:24]=[CH:23][C:22]([NH:25][C:26](=[O:28])[CH3:27])=[C:21]([OH:29])[CH:20]=1.C([O-])([O-])=O.[Cs+].[Cs+]>CN(C=O)C>[Cl:18][C:19]1[CH:24]=[CH:23][C:22]([NH:25][C:26](=[O:28])[CH3:27])=[C:21]([O:29][CH2:4][C@@H:2]2[CH2:3][O:1]2)[CH:20]=1

参加物

5

反応物 3

HCID 10796Cesium carbonateHCID 146490Benzenesulfonic acid, 3-nitro-, (2S)-2-oxiranylmethyl esterHCID 177739N-(4-Chloro-2-hydroxyphenyl)acetamide

生成物 1

HCID 86601481N-{4-Chloro-2-[(2S)-oxiran-2-ylmethoxy]phenyl}acetamide収率 73.7%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
0 °C

実験手順

To a mixture of (2S)-oxiran-2ylmethyl3-nitrobenzenesulfonate (3.37 g, 13.25 mmol), N-(4-chloro-2-hydroxyphenyl)acetamide (2.46 g, 17.23 mmol) and Cs2CO3 (6.48 g, 19.88 mmol) was added DMF (20 mL) at 0° C. and the reaction mixture was stirred at 0° C. for 3 h. The reaction mixture was partitioned between ethyl acetate and water. The organic layer was dried over Na2SO4, filtered and concentrated. The residue was purified by silica gel flash chromatography (hexane:ethyl acetate 3:2) to give the subtitled compound (2.36 g).

後処理

  1. customThe reaction mixture was partitioned between ethyl acetate and water
  2. dry with materialThe organic layer was dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe residue was purified by silica gel flash chromatography (hexane:ethyl acetate 3:2)

出典と根拠

ORDレコード
ord-62d08c44daf2470caad11857e41ea86f
出典データセット
uspto-grants-2008_11
特許番号
US07449475B2

関連ノート

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