Cesium carbonate → N-Cyclopropyl-4-fluoro-2-(2-oxiranylmethoxy)benzamide

HRID 270064ノート

反応式

HRID 270064 の反応式
[CH:1]1([NH:4][C:5](=[O:14])[C:6]2[CH:11]=[CH:10][C:9]([F:12])=[CH:8][C:7]=2[OH:13])[CH2:3][CH2:2]1.[O:15]1[CH2:17][C@H:16]1[CH2:18]OS(C1C=CC=C([N+]([O-])=O)C=1)(=O)=O.C([O-])([O-])=O.[Cs+].[Cs+]>CN(C=O)C>[CH:1]1([NH:4][C:5](=[O:14])[C:6]2[CH:11]=[CH:10][C:9]([F:12])=[CH:8][C:7]=2[O:13][CH2:18][CH:16]2[CH2:17][O:15]2)[CH2:2][CH2:3]1

参加物

5

反応物 3

HCID 10796Cesium carbonateHCID 146490Benzenesulfonic acid, 3-nitro-, (2S)-2-oxiranylmethyl esterHCID 68961144N-Cyclopropyl-4-fluoro-2-hydroxybenzamide

生成物 1

HCID 45086863N-Cyclopropyl-4-fluoro-2-(2-oxiranylmethoxy)benzamide収率 59.7%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

A mixturte of N-cyclopropyl-4-fluoro-2-hydroxybenzamide (195 mg, 1.0 mmol), (2S)-oxiran-2-ylmethyl3-nitrobenzenesulfonate (259 mg, 1.0 mmol) and Cs2CO3 (390 mg, 1.2 mmol) in DMF (5 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 (0-30% ethylacetate in petroleum ether) to give the subtitled compound (150 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 (0-30% ethylacetate in petroleum ether)

出典と根拠

ORDレコード
ord-b7e30bb29ea445ab83e4de635ec2c63e
出典データセット
uspto-grants-2008_11
特許番号
US07449475B2

反応ノート

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