Potassium Carbonate → 4-Bromo-3-{[(2,4-dimethoxy-benzyl)-methoxycarbonylmethyl-amino]-methyl}-thiophene-2-carboxylic acid methyl ester

HRID 1465950ノート

反応式

HRID 1465950 の反応式
[CH3:1][O:2][C:3]([C:5]1[S:6][CH:7]=[C:8]([Br:12])[C:9]=1[CH2:10]Br)=[O:4].[CH2:13]([O:15][C:16](=[O:30])[CH2:17][NH:18][CH2:19][C:20]1[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[CH:22][C:21]=1[O:28][CH3:29])C.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O.C(OCC)(=O)C>[CH3:1][O:2][C:3]([C:5]1[S:6][CH:7]=[C:8]([Br:12])[C:9]=1[CH2:10][N:18]([CH2:19][C:20]1[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[CH:22][C:21]=1[O:28][CH3:29])[CH2:17][C:16]([O:15][CH3:13])=[O:30])=[O:4]

参加物

6

反応物 3

HCID 11430Potassium CarbonateHCID 19895532Ethyl 2-(2,4-dimethoxybenzylamino)acetateHCID 67233904Methyl 4-bromo-3-(bromomethyl)thiophene-2-carboxylate

生成物 1

HCID 672333554-Bromo-3-{[(2,4-dimethoxy-benzyl)-methoxycarbonylmethyl-amino]-methyl}-thiophene-2-carboxylic acid methyl ester収率 92.1%

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

実験手順

4-Bromo-3-bromomethyl-thiophene-2-carboxylic acid methyl ester (2.28 g, 7.31 mmol), example 31-b, was dissolved in 18 mL of dry N,N-dimethylformamide. N-(2,4-dimethoxy-benzyl)glycine ethyl ester (1.75 g, 7.31 mmol) and potassium carbonate (1.11 g, 8.04 mmol) were added and the reaction mixture was stirred at room temperature for 18 hours. The reaction mixture was diluted with ethyl acetate and washed with water and brine. The organic fraction was dried over anhydrous sodium sulfate, and concentrated. The crude product was purified by flash chromatography eluting from silica gel with a gradient of 0-60% ethyl acetate in hexanes to produce 3.18 g of a tan oil. MS: (+) m/z 494.1, 496.1 (M+Na+, 79Br/81Br).

後処理

  1. washwashed with water and brine
  2. dry with materialThe organic fraction was dried over anhydrous sodium sulfate
  3. concentrationconcentrated
  4. customThe crude product was purified by flash chromatography
  5. washeluting from silica gel with a gradient of 0-60% ethyl acetate in hexanes

出典と根拠

ORDレコード
ord-287ef8af6cc34f0eabbf9e7b2488d232
出典データセット
uspto-grants-2015_04
特許番号
US09000006B2

反応ノート

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