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

HRID 270064노트

반응식

HRID 270064 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-b7e30bb29ea445ab83e4de635ec2c63e
출처 데이터셋
uspto-grants-2008_11
특허 번호
US07449475B2

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