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

HRID 1923980Notes

Reaction equation

HRID 1923980 reaction equation
[NH:1]([CH2:6][C:7]([OH:9])=[O:8])[CH2:2][C:3]([OH:5])=[O:4].C([O-])([O-])=O.[K+].[K+].C1C(=O)N([O:23][C:24]([O:26][CH2:27][C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)=O)C(=O)C1>O.CC(C)=O>[CH2:27]([O:26][C:24]([N:1]([CH2:6][C:7]([OH:9])=[O:8])[CH2:2][C:3]([OH:5])=[O:4])=[O:23])[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1

Participants

6

Reactant 3

HCID 8897Iminodiacetic acidHCID 11430Potassium CarbonateHCID 83172Benzyl succinimido carbonate

Product 1

HCID 10107013N-(Carboxymethyl)-N-((phenylmethoxy)carbonyl)glycineYield 75%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent

Procedure

To the solution of iminodiacetic acid XLV (10 g, 75.13 mmol) and K2CO3 (41.53 g, 300.52 mmol) in water (225 mL) was added a solution of CBzOsu (20.6 g, 82.64 mmol) in acetone (150 mL). The mixture was stirred at r.t. overnight. The acetone was evaporated under reduced pressure and the remaining water was washed with ethyl ether (2×). The aqueous layer was acidified to pH=2 with 2 M aq. HCl and then saturated with NaCl, washed with EtOAc (3×). The combined EtOAc was dried over MgSO4 and evaporated under reduced pressure to give 2-{[(benzyloxy)carbonyl](carboxymethyl) amino}acetic acid XLVI (15 g, 56.17 mmol, 75% yield). ESIMS found for C12H13NO6 m/z 290 (M+Na).

Workup

  1. customThe acetone was evaporated under reduced pressure
  2. washthe remaining water was washed with ethyl ether (2×)
  3. washsaturated with NaCl, washed with EtOAc (3×)
  4. dry with materialThe combined EtOAc was dried over MgSO4
  5. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-cdbd9fda29eb449ba9c028322f14f9f8
Source dataset
uspto-grants-2012_05
Patent number
US08178490B2

Reaction notes

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