[N-benzyl-N-(2-hydroxybutyl)amino]acetic acid → (2-Hydroxybutylamino)acetic acid

HRID 480589Notes

Reaction equation

HRID 480589 reaction equation
C([N:8]([CH2:14][C:15]([OH:17])=[O:16])[CH2:9][CH:10]([OH:13])[CH2:11][CH3:12])C1C=CC=CC=1.C(#N)C.O.FC(F)(F)C(O)=O>CO.O.[Pd].[H][H]>[OH:13][CH:10]([CH2:11][CH3:12])[CH2:9][NH:8][CH2:14][C:15]([OH:17])=[O:16]

Participants

7

Reactant 2

HCID 18765602[N-benzyl-N-(2-hydroxybutyl)amino]acetic acidHCID 22145617Water TFA acetonitrile

Product 1

HCID 18765545(2-Hydroxybutylamino)acetic acid

Reagents, catalysts & solvents 4

HCID 887MethanolSolventHCID 962WaterSolventHCID 23938PalladiumSolventHCID 178418361HCID 178418361, compoundSolvent

Procedure

4.60 g of [N-benzyl-N-(2-hydroxybutyl)amino]acetic acid are dissolved in a mixture of methanol and water (7:1) and hydrogenated in the presence of palladium (10% on activated charcoal) as catalyst for about 2.5 hours at ambient temperature until the calculated amount of hydrogen has been taken up. For working up, the catalyst is filtered off and the filtrate evaporated down in vacuo, leaving a white solid. Yield: 2.77 g (97% of theory); Rf value: 0.86 (Reversed phase ready-made TLC plate (E. Merck), acetonitrile/water/trifluoroacetic acid=50:50:1); mass spectrum (ESI−): m/z=146 [M−H]−.

Workup

  1. filtrationthe catalyst is filtered off
  2. customthe filtrate evaporated down in vacuo
  3. customleaving a white solid

Sources & evidence

ORD record
ord-f1549433c1e842168323583fa338fcdc
Source dataset
uspto-grants-2003_11
Patent number
US06653305B2

Reaction notes

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