2-Bromobenzyl bromide → 3-[3-(2-Bromobenzyl)-3H-imidazol-4-yl]propionic acid methyl ester

HRID 76892

反応式

HRID 76892 の反応式
[CH3:1][O:2][C:3](=[O:30])[CH2:4][CH2:5][C:6]1[N:7]=[CH:8][N:9](C(C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[CH:10]=1.[Br:31][C:32]1[CH:39]=[CH:38][CH:37]=[CH:36][C:33]=1[CH2:34]Br>CC#N.CCOC(C)=O>[CH3:1][O:2][C:3](=[O:30])[CH2:4][CH2:5][C:6]1[N:7]([CH2:34][C:33]2[CH:36]=[CH:37][CH:38]=[CH:39][C:32]=2[Br:31])[CH:8]=[N:9][CH:10]=1

参加物

5

反応物 2

HCID 769652-Bromobenzyl bromideHCID 10475868Methyl 3-(1-Tritylimidazol-4-yl) Propionate

生成物 1

HCID 588271303-[3-(2-Bromobenzyl)-3H-imidazol-4-yl]propionic acid methyl ester

試薬・触媒・溶媒 2

HCID 6342Acetonitrile溶媒2 回HCID 8857Ethyl Acetate溶媒

実験手順

To a solution of 3-(1-trityl-1H-imidazol-4-yl)propanoic acid methyl ester (5.0 g, 12.6 mmol) in CH3CN (80 mL) is added a solution of 2-bromobenzylbromide (2.84 g, 11.4 mmol) in CH3CN (20 mL). The resulting clear solution is stirred at ambient temperature over the weekend. The mixture is concentrated and the remaining oil is taken up in 85 mL methanol and heated up at 70° C. for 2 h. Then the mixture is concentrated to give a yellow oil, which is taken up in EtOAc and washed with saturated aqueous NaHCO3 and brine, dried over anhydrous Na2SO4, and concentrated to yield a viscous oil. The crude reaction mixture is subjected to flash chromatography (silica gel) eluting with MeOH:CH2Cl2 to give the desired compound. MS (ESI) m/z 323 (M+H).

後処理

  1. concentrationThe mixture is concentrated
  2. temperatureheated up at 70° C. for 2 h
  3. concentrationThen the mixture is concentrated
  4. customto give a yellow oil, which
  5. washwashed with saturated aqueous NaHCO3 and brine
  6. dry with materialdried over anhydrous Na2SO4
  7. concentrationconcentrated
  8. customto yield a viscous oil
  9. customThe crude reaction mixture
  10. washeluting with MeOH

出典と根拠

ORDレコード
ord-b41e2132a9a845cb9b032efa260435e5
出典データセット
uspto-grants-2014_09
特許番号
US08835646B2

関連ノート

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