Dichloromethane → N-Benzylglycine ethyl ester

HRID 18815

반응식

HRID 18815 반응식
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]

참가 물질

6

반응물 4

HCID 6344DichloromethaneHCID 7504BenzylamineHCID 7748Ethyl bromoacetateHCID 81531Diisopropylethylamine

생성물 1

HCID 80908N-Benzylglycine ethyl ester수율 75%

시약·촉매·용매 1

HCID 312751,4-Dioxane용매

반응 조건

온도
90 °C

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-8f0bf5e36b304a20b2feff7f945e6f61
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07741493B2

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