Triethylamine → HCID 62499585, compound

HRID 1408185Notes

Reaction equation

HRID 1408185 reaction equation
[NH2:1][CH2:2][CH2:3][O:4][CH2:5][CH2:6][OH:7].Br[CH2:9][C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11].C(N(CC)CC)C>C1COCC1>[OH:7][CH2:6][CH2:5][O:4][CH2:3][CH2:2][NH:1][CH2:9][C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 13578DiglycolamineHCID 79177tert-Butyl bromoacetate

Product 1

HCID 62499585HCID 62499585, compoundYield 23.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

2-(2-aminoethoxy)ethanol (11 g, 104.62 mmol, 1.00 equiv) was dissolved in THF (300 mL) and cooled to 0° C. To the stirring solution was added dropwise tert-butyl 2-bromoacetate (20 g, 102.54 mmol, 1.00 equiv) and then triethylamine (15.5 g, 153.18 mmol, 1.50 equiv) dropwise The solution was then stirred for 16 h at room temperature. The solvent was removed and the residue then dissolved in DCM and washed twice with brine, then dried over anhydrous sodium sulfate and solvent removed. The residue was applied onto a silica gel column with dichloromethane/methanol (20:1) as eluent. This resulted in 5.25 g (16%) of the product as a yellow oil. MS (ES, m/z) 220 [M+H]+

Workup

  1. customThe solvent was removed
  2. dissolutionthe residue then dissolved in DCM
  3. washwashed twice with brine
  4. dry with materialdried over anhydrous sodium sulfate and solvent
  5. customremoved

Sources & evidence

ORD record
ord-d176e93c9e434c26972a4e1f4fcc7d07
Source dataset
uspto-grants-2014_12
Patent number
US08916569B2

Reaction notes

Loading…