Water → N-(Bromoacetyl)glycine, ethyl ester

HRID 240321Notes

Reaction equation

HRID 240321 reaction equation
Cl.[CH2:2]([O:4][C:5](=[O:8])[CH2:6][NH2:7])[CH3:3].C([O-])([O-])=O.[K+].[K+].[Br:15][CH2:16][C:17](Br)=[O:18].O>C(Cl)Cl>[CH2:2]([O:4][C:5](=[O:8])[CH2:6][NH:7][C:17](=[O:18])[CH2:16][Br:15])[CH3:3]

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 61147Bromoacetyl bromideHCID 2723640Glycine ethyl ester, hydrochloride

Product 1

HCID 96555N-(Bromoacetyl)glycine, ethyl esterYield 40%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mixture of glycine ethyl ester hydrochloride (2.0 g, 14.3 mmol) and K2CO3 (2.1 g, 15.2 mmol) in CH2Cl2 (35 ml) cooled at 0-5° C. bromoacetyl bromide (1.36 ml, 15.6 mmol) was added dropwise. The suspension was stirred at room temperature and after 3 h H2O (20 ml) was added. The phases were separated and the organic one was washed with a saturated solution of NaHCO3 (20 ml) and H2O (20 ml) and dried over Na2SO4. The solvent was evaporated obtaining 39 as white solid (1.2 g, 40%). ESI+MS: calcd for C6H10BrNO3: 224.06; found: 224.0 and 226.0 (MH+).

Workup

  1. additionwas added dropwise
  2. additionwas added
  3. customThe phases were separated
  4. washthe organic one was washed with a saturated solution of NaHCO3 (20 ml) and H2O (20 ml)
  5. dry with materialdried over Na2SO4
  6. customThe solvent was evaporated

Sources & evidence

ORD record
ord-85f3c0cf834d41b9a0e7d9c94b7c9c19
Source dataset
uspto-grants-2014_02
Patent number
US08648076B2

Reaction notes

Loading…