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

HRID 1469718ノート

反応式

HRID 1469718 の反応式
[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]

参加物

6

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-ebb8759a32ff44b8be66a10cea2d4e20
出典データセット
uspto-grants-2015_04
特許番号
US09006257B2

反応ノート

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