Cesium carbonate → Methyl 4-fluoro-2-[(2S)-oxiran-2-ylmethoxy]benzoate

HRID 270105노트

반응식

HRID 270105 반응식
[F:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[C:4]([OH:12])[CH:3]=1.[N+](C1C=C(S(O[CH2:26][C@@H:27]2[CH2:29][O:28]2)(=O)=O)C=CC=1)([O-])=O.C([O-])([O-])=O.[Cs+].[Cs+]>CN(C=O)C>[F:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[C:4]([O:12][CH2:26][C@@H:27]2[CH2:29][O:28]2)[CH:3]=1

참가 물질

5

반응물 3

HCID 10796Cesium carbonateHCID 146490Benzenesulfonic acid, 3-nitro-, (2S)-2-oxiranylmethyl esterHCID 2775386Methyl 4-fluorosalicylate

생성물 1

HCID 71655301Methyl 4-fluoro-2-[(2S)-oxiran-2-ylmethoxy]benzoate수율 96.7%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

A mixture of methyl 4-fluoro-2-hydroxybenzoate (456.3 mg, 1.76 mmol), (2S)-oxiran-2-ylmethyl 3-nitrobenzenesulfonate (300 mg, 1.76 mmol) and Cs2CO3 (687.4 mg, 2.11 mmol) in DMF (4.5 mL) was stirred at room temperature overnight. The reaction mixture was partitioned between ethyl acetate and H2O, organic layer was dried over Na2SO4, filtered and concentrated in vacuo. The residue was opurified by silica gel flash chromatography (0-30% ethyl acetate in petroleum spirit) to give the subtitled compound (385 mg).

후처리

  1. customThe reaction mixture was partitioned between ethyl acetate and H2O, organic layer
  2. dry with materialwas dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-a3296f6dec6e49f29eb1e5ed177a23ad
출처 데이터셋
uspto-grants-2008_11
특허 번호
US07449475B2

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