Dichloromethane → N-Benzylglycine ethyl ester

HRID 18815

Reaction equation

HRID 18815 reaction equation
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]

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 7504BenzylamineHCID 7748Ethyl bromoacetateHCID 81531Diisopropylethylamine

Product 1

HCID 80908N-Benzylglycine ethyl esterYield 75%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
90 °C

Procedure

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).

Workup

  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)

Sources & evidence

ORD record
ord-8f0bf5e36b304a20b2feff7f945e6f61
Source dataset
uspto-grants-2010_06
Patent number
US07741493B2

Linked notes

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