Cesium carbonate → HCID 86601480、化合物

HRID 270072

反応式

HRID 270072 の反応式
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([OH:12])=[C:6]([NH:8][C:9](=[O:11])[CH3:10])[CH:7]=1.[O:13]1[CH2:15][C@H:14]1[CH2:16]OS(C1C=CC=C([N+]([O-])=O)C=1)(=O)=O.C([O-])([O-])=O.[Cs+].[Cs+]>CN(C=O)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:12][CH2:16][C@@H:14]2[CH2:15][O:13]2)=[C:6]([NH:8][C:9](=[O:11])[CH3:10])[CH:7]=1

参加物

5

反応物 3

HCID 10796Cesium carbonateHCID 952582-Acetylamino-4-chlorophenolHCID 146490Benzenesulfonic acid, 3-nitro-, (2S)-2-oxiranylmethyl ester

生成物 1

HCID 86601480HCID 86601480、化合物収率 92.3%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

A mixture of N-(5-chloro-2-hydroxyphenyl)acetamide (500 mg, 2.69 mmol), (2S)-oxiran-2-ylmethyl3-nitrobenzenesulfonate (697 mg, 2.69 mmol) and Cs2CO3 (1.04 g, 3.22 mmol) in DMF (10 mL) was stirred at room temperature overnight. 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 (0-50% ethyl acetate in petroleum ether) to give the subtitled compound (600 mg).

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 (0-50% ethyl acetate in petroleum ether)

出典と根拠

ORDレコード
ord-ba1e445f47844faaa2ea1eba40902c38
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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