Dichloromethane → N-Benzylglycine ethyl ester

HRID 18815

反応式

HRID 18815 の反応式
Br[CH2:2][C:3]([O:5][CH2:6][CH3:7])=[O:4].C(N(CC)C(C)C)(C)C.[CH2:17]([NH2:24])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.ClCCl>O1CCOCC1>[CH2:6]([O:5][C:3](=[O:4])[CH2:2][NH:24][CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[CH3:7]

参加物

6

反応物 4

HCID 6344DichloromethaneHCID 7504BenzylamineHCID 7748Ethyl bromoacetateHCID 81531Diisopropylethylamine

生成物 1

HCID 80908N-Benzylglycine ethyl ester収率 75%

試薬・触媒・溶媒 1

HCID 312751,4-Dioxane溶媒

反応条件

温度
90 °C

実験手順

To a solution of ethyl bromoacetate (2.22 mL, 20.0 mmol) in 1,4-dioxane (40 mL) is added N,N-diisopropylethylamine (7.0 mL, 40.0 mol) and benzylamine (3.3 mL, 30.0 mmol), and the mixture is heated at 90° C. for 3 h. The reaction mixture is cooled to RT, dichloromethane is added, and the solution is washed with water, brine, then dried (MgSO4), and filtered. The filtrate is evaporated, and the residue is residue purified by chromatography on silica gel; elution with EtOAc:MeOH:heptane (35:5:60) gives 2.9 g of the product 421. 1H NMR (CDCl3) δ 7.4-7.3 (m, 6 H), 4.19 (q, 2 H), 3.80 (s, 2 H), 3.40 (s, 2 H), 1.25 (t, 3 H); MS: m/z 194 (M++1).

後処理

  1. temperatureThe reaction mixture is cooled to RT
  2. washthe solution is washed with water, brine
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. customThe filtrate is evaporated
  6. custompurified by chromatography on silica gel
  7. washelution with EtOAc:MeOH:heptane (35:5:60)

出典と根拠

ORDレコード
ord-8f0bf5e36b304a20b2feff7f945e6f61
出典データセット
uspto-grants-2010_06
特許番号
US07741493B2

関連ノート

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