Methyl iodide → Methyl 5-[(tert-butoxycarbonylamino)methyl]-2-chloro-benzoate

HRID 1469718노트

반응식

HRID 1469718 반응식
[C:1]([O:5][C:6]([NH:8][CH2:9][C:10]1[CH:11]=[CH:12][C:13]([Cl:19])=[C:14]([CH:18]=1)[C:15]([OH:17])=[O:16])=[O:7])([CH3:4])([CH3:3])[CH3:2].CI.[C:22]([O-])([O-])=O.[K+].[K+]>CN(C=O)C.CCOC(C)=O>[C:1]([O:5][C:6]([NH:8][CH2:9][C:10]1[CH:11]=[CH:12][C:13]([Cl:19])=[C:14]([CH:18]=1)[C:15]([O:17][CH3:22])=[O:16])=[O:7])([CH3:4])([CH3:2])[CH3:3]

참가 물질

6

반응물 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 584833575-(((tert-Butoxycarbonyl)amino)methyl)-2-chlorobenzoic acid

생성물 1

HCID 86692228Methyl 5-[(tert-butoxycarbonylamino)methyl]-2-chloro-benzoate수율 41.9%

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

실험 절차

To a solution of 5-{[(tert-butoxycarbonyl)amino]methyl}-2-chlorobenzoic acid (1.0 g, 3.50 mmol) in DMF (5.0 mL) were added methyl iodide (496 mg, 3.50 mmol) and K2CO3 (966 mg, 7.00 mmol). The reaction mass was stirred at rt for 18 h. The reaction mass was diluted with EtOAc and the organic layer was washed with water and brine. The organic layer was separated, dried, filtered and concentrated. The concentrate was purified by column chromatography to afford 440 mg of the title product. 1H NMR (300 MHz, DMSO d6): δ 7.66 (s, 1H), 7.49-7.52 (m, 2H), 7.42 (d, J=6.3 Hz, 1H), 4.13 (d, J=5.7 Hz, 2H), 3.85 (s, 3H), 1.38 (s, 9H).

후처리

  1. washthe organic layer was washed with water and brine
  2. customThe organic layer was separated
  3. customdried
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe concentrate was purified by column chromatography

출처 및 근거

ORD 기록
ord-ebb8759a32ff44b8be66a10cea2d4e20
출처 데이터셋
uspto-grants-2015_04
특허 번호
US09006257B2

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