Hydrochloric Acid → Iminodiacetic acid

HRID 1740725Notes

Reaction equation

HRID 1740725 reaction equation
C([O:8][C:9](=[O:30])[CH2:10][NH:11][CH:12](C(OC(C)(C)C)=O)[C:13]([O:15]CC1C=CC=CC=1)=[O:14])C1C=CC=CC=1.Cl.CCOCC>O1CCOCC1>[NH:11]([CH2:12][C:13]([OH:15])=[O:14])[CH2:10][C:9]([OH:30])=[O:8]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 86754660Boc-Iminodiacetic acid dibenzyl ester

Product 1

HCID 8897Iminodiacetic acidYield 247.2%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

Boc-Iminodiacetic acid dibenzyl ester (4.5 g, 10.88 mmol) was dissolved in dioxane (15 mL), then 4.6 M HCl in dioxane (20 mL) was added. The mixture was stirred for 90 min at room temperature and Et2O (200 mL) was added. The crystalline product was filtered off, washed twice with Et2O and dried in vacuo to afford the title compound (3.58 g, 94.2%).

Workup

  1. filtrationThe crystalline product was filtered off
  2. washwashed twice with Et2O
  3. customdried in vacuo

Sources & evidence

ORD record
ord-10908730324d424f8aa68cdaba17a4a7
Source dataset
uspto-grants-1999_10
Patent number
US05972926

Reaction notes

Loading…