Dichloromethane → N-Benzylglycine ethyl ester

HRID 2053606Notes

Reaction equation

HRID 2053606 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, 6H), 4.19 (q, 2H), 3.80 (s, 2H), 3.40 (s, 2H), 1.25 (t, 3H); 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-80112058dff348348927ff1cd29b0dd6
Source dataset
uspto-grants-2008_02
Patent number
US07326792B2

Reaction notes

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