Methanesulfonyl chloride → 3-Acetamido-6-chloro-2-fluorobenzyl methanesulfonate

HRID 1257163노트

반응식

HRID 1257163 반응식
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9](=[O:11])[CH3:10])=[C:4]([F:12])[C:3]=1[CH2:13][OH:14].[CH3:15][S:16](Cl)(=[O:18])=[O:17]>C(Cl)Cl>[CH3:15][S:16]([O:14][CH2:13][C:3]1[C:2]([Cl:1])=[CH:7][CH:6]=[C:5]([NH:8][C:9](=[O:11])[CH3:10])[C:4]=1[F:12])(=[O:18])=[O:17]

참가 물질

4

반응물 2

HCID 31297Methanesulfonyl chlorideHCID 86713625N-(4-chloro-2-fluoro-3-(hydroxymethyl)phenyl)acetamide

생성물 1

HCID 867136263-Acetamido-6-chloro-2-fluorobenzyl methanesulfonate수율 91.9%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

A 0° C. of N-(4-chloro-2-fluoro-3-(hydroxymethyl)phenyl)acetamide (1.05 g, 4.82 mmol) and TEA (1.003 mL, 7.24 mmol) in DCM (30 mL) was treated slowly with methanesulfonyl chloride (0.414 mL, 5.31 mmol), warmed to RT and stirred for 2 h. The mixture was treated with satd. NaHCO3, extracted with DCM (2×) and the combined organics were washed with brine, dried over Na2SO4 and concentrated to dryness to afford 3-acetamido-6-chloro-2-fluorobenzyl methanesulfonate (1.31 g, 74% yield) as an off-white solid. MS (ESI) m/z: 296.0 [M+H]+.

후처리

  1. additionThe mixture was treated with satd
  2. extractionNaHCO3, extracted with DCM (2×)
  3. washthe combined organics were washed with brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated to dryness

출처 및 근거

ORD 기록
ord-b6cd181252794d948d2e9d900a4deed8
출처 데이터셋
uspto-grants-2013_06
특허 번호
US08461179B1

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