Ethyl bromoacetate → HCID 22080505, compound

HRID 1591960Notes

Reaction equation

HRID 1591960 reaction equation
[NH2:1][CH2:2][C:3]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH:6]=[CH:5][CH:4]=1.Br[CH2:14][C:15]([O:17][CH2:18][CH3:19])=[O:16]>C(Cl)Cl>[CH2:18]([O:17][C:15](=[O:16])[CH2:14][NH:1][CH2:2][C:3]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH:6]=[CH:5][CH:4]=1)[CH3:19]

Participants

4

Reactant 2

HCID 7748Ethyl bromoacetateHCID 83551-Naphthalenemethanamine

Product 1

HCID 22080505HCID 22080505, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 1-aminomethylnaphthalene (2.15 g, 13.6 mmol) and TEA (1.65 g, 16.3 mmol) in CH2Cl2 (50 mL) is treated with ethyl bromoacetate (2.28 g, 13.6 mmol) dropwise over 90 min. The mixture is stirred at RT for 3 h and washed with water. The organic layer is dried over anhydrous MgSO4 and concentrated. The residue is flash chromatographed on silica gel using CH2Cl2→1% MeOH in CH2Cl2 as the eluent to afford N-(1-naphthyl-methyl)-glycine ethyl ester as a yellow oil: [M+1]+=244.

Workup

  1. washwashed with water
  2. dry with materialThe organic layer is dried over anhydrous MgSO4
  3. concentrationconcentrated
  4. customchromatographed on silica gel

Sources & evidence

ORD record
ord-5b7fa37eff5a4cb299db6a08c1df7799
Source dataset
uspto-grants-2007_11
Patent number
US07291635B2

Reaction notes

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