Pyridine → Phenyl 3-fluoro-4-(methylsulfonamidomethyl)phenylcarbamate

HRID 1428740노트

반응식

HRID 1428740 반응식
[NH2:1][C:2]1[CH:13]=[CH:12][C:5]([CH2:6][NH:7][S:8]([CH3:11])(=[O:10])=[O:9])=[C:4]([F:14])[CH:3]=1.[C:15]1([O:21][C:22](Cl)=[O:23])[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.N1C=CC=CC=1>O1CCCC1.C(#N)C.C(OCC)(=O)C>[F:14][C:4]1[CH:3]=[C:2]([NH:1][C:22](=[O:23])[O:21][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH:13]=[CH:12][C:5]=1[CH2:6][NH:7][S:8]([CH3:11])(=[O:10])=[O:9]

참가 물질

7

반응물 3

HCID 1049PyridineHCID 15891Phenyl chloroformateHCID 86679367N-(4-amino-2-fluorobenzyl)methanesulfonamide

생성물 1

HCID 86679368Phenyl 3-fluoro-4-(methylsulfonamidomethyl)phenylcarbamate수율 85%

시약·촉매·용매 3

HCID 6342Acetonitrile용매HCID 8028Tetrahydrofuran용매HCID 8857Ethyl Acetate용매

실험 절차

To a stirred solution of N-(4-amino-2-fluorobenzyl)methanesulfonamide (190 mg, 0.871 mmol) in tetrahydrofuran and acetonitrile as co-solvent were added phenylchloroformate (0.115 ml, 0.914 mmol) and pyridine (0.084 ml, 1.045 mmol). The reaction mixture was stirred for 1 h at room temperature. The mixture dissolved in ethyl acetate and washed with water and brine. The organic layer was dried over magnesium sulfate and filtered. The filtrate was removed in vacuo. The crude was purified by column chromatography. Phenyl 3-fluoro-4-(methylsulfonamidomethyl)phenylcarbamate (250 mg) was obtained as 85% yield.

후처리

  1. washwashed with water and brine
  2. dry with materialThe organic layer was dried over magnesium sulfate
  3. filtrationfiltered
  4. customThe filtrate was removed in vacuo
  5. customThe crude was purified by column chromatography

출처 및 근거

ORD 기록
ord-ecfd50b90de44a79ae2b49c635cca9b9
출처 데이터셋
uspto-grants-2015_01
특허 번호
US08937092B2

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