Glycine → Glycine, N-dodecyl-

HRID 36316

Reaction equation

HRID 36316 reaction equation
[NH2:1][CH2:2][C:3]([OH:5])=[O:4].C(N(CC)CC)C.Br[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25]>CC(O)C.O>[CH2:25]([NH:1][CH2:2][C:3]([OH:5])=[O:4])[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20][CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][CH3:14]

Participants

6

Reactant 3

HCID 750GlycineHCID 8471TriethylamineHCID 89191-Bromododecane

Product 1

HCID 16771Glycine, N-dodecyl-Yield 26.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3776IsopropanolSolvent

Procedure

Glycine was dissolved in a 2:1 mixture by volume of IPA and water. Triethylamine and 1-bromododecane were added to the solution successively and the mixture was kept stirring for more than 7 days. After the solvent was removed, THF was added to the remaining material. Triethylamine hydrobromide was removed by filtration and the filtrate was concentrated. N-n-dodecylglycine was obtained from the concentrated solution by separation and purification by column chromatography with the yield of 26.3%.

Workup

  1. customAfter the solvent was removed
  2. additionTHF was added to the remaining material
  3. customTriethylamine hydrobromide was removed by filtration
  4. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-2d8987052d2b49178f764ccb79a5ad51
Source dataset
uspto-grants-1995_05
Patent number
US05413794

Linked notes

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