Ethyl bromoacetate → HCID 11679939, compound

HRID 556453Notes

Reaction equation

HRID 556453 reaction equation
[CH:1]1([NH2:7])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[CH2:8]([O:10][C:11](=[O:14])[CH2:12]Br)[CH3:9]>ClCCl>[CH2:8]([O:10][C:11](=[O:14])[CH2:12][NH:7][CH:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1)[CH3:9]

Participants

4

Reactant 2

HCID 7748Ethyl bromoacetateHCID 7965Cyclohexylamine

Product 1

HCID 11679939HCID 11679939, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of cyclohexylamine (45 g, 0.45 mol) in dichloromethane (100 mL) was slowly added bromo-acetic acid ethyl ester (15 g, 0.09 mol) in dichloromethane (150 mL) at 0° C. After the addition, the mixture was stirred at room temperature for 1 h and then washed with water (3×200 mL). The organic solution was dried with Na2SO4 and concentrated in vacuo. The residue was purified with chromatography (DCM: MeOH=30:1) to give cyclohexylamino-acetic acid ethyl ester as an oil. MS: 186 (M+H)+.

Workup

  1. customat 0° C
  2. additionAfter the addition
  3. washwashed with water (3×200 mL)
  4. dry with materialThe organic solution was dried with Na2SO4
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified with chromatography (DCM: MeOH=30:1)

Sources & evidence

ORD record
ord-3169c52382bc453f8535be98c740fd66
Source dataset
uspto-grants-2011_11
Patent number
US08058269B2

Reaction notes

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