Iminodiacetic acid → N-(Carboxymethyl)-N-((phenylmethoxy)carbonyl)glycine

HRID 2114846Notes

Reaction equation

HRID 2114846 reaction equation
[C:1]([CH2:4][NH:5][CH2:6][C:7]([OH:9])=[O:8])([OH:3])=[O:2].[CH2:10]([O:17][C:18](Cl)=[O:19])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1>[OH-].[Na+]>[CH2:10]([O:17][C:18]([N:5]([CH2:6][C:7]([OH:9])=[O:8])[CH2:4][C:1]([OH:3])=[O:2])=[O:19])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

4

Reactant 2

HCID 8897Iminodiacetic acidHCID 10387Benzyl chloroformate

Product 1

HCID 10107013N-(Carboxymethyl)-N-((phenylmethoxy)carbonyl)glycine

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent2×

Procedure

To a solution of N-(carboxymethyl)glycine (13.31 g, 100.00 mmol) in aqueous 2N NaOH (100 mL) was added a solution of benzylchloroformate (18.77 g, 110.00 mmol) in aqueous 2N NaOH (55 mL) at 0° C. The reaction was stirred at room temperature overnight and washed with Et2O. The aqueous layer was acidified to pH 2 with aqueous 1N HCl solution and extracted four times with Et2O. The combined organic layers were dried over MgSO4, filtered, and concentrated in vacuo to afford the product as a clear oil.

Workup

  1. washwashed with Et2O
  2. extractionextracted four times with Et2O
  3. dry with materialThe combined organic layers were dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-c78007b19ff9406598aa014bf1b61aea
Source dataset
uspto-grants-2008_10
Patent number
US07435735B2

Reaction notes

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