Hydrochloric Acid → Iminodiacetic acid

HRID 1954849Notes

Reaction equation

HRID 1954849 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-d6abcf194b374ed8a9eea0430cb9b194
Source dataset
uspto-grants-2000_09
Patent number
US06124298

Reaction notes

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