Tetrahydrofuran → N-(tert-Butoxycarbonyl)iminodiacetic Acid

HRID 853634Notes

Reaction equation

HRID 853634 reaction equation
[NH:1]([CH2:6][C:7]([OH:9])=[O:8])[CH2:2][C:3]([OH:5])=[O:4].C(=O)([O-])O.[Na+].C1COCC1.[O:20](C(OC(C)(C)C)=O)[C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=O>O>[C:24]([O:23][C:21]([N:1]([CH2:6][C:7]([OH:9])=[O:8])[CH2:2][C:3]([OH:5])=[O:4])=[O:20])([CH3:27])([CH3:26])[CH3:25]

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 8897Iminodiacetic acidHCID 90495Di-tert-butyl dicarbonateHCID 516892Sodium Bicarbonate

Product 1

HCID 2755971N-(tert-Butoxycarbonyl)iminodiacetic Acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of iminodiacetic acid (5.1 g, 38.3 mmol) and sodium hydrogen carbonate (NaHCO3, 12.9 g, 153 mmol) were dissolved in 50 mL of water. Once the bubbling subsided, 50 mL of THF was added followed by 10.0 g (46.0 mmol) of BOC2O. The mixture was stirred at ambient temperature for 2 days when starting materials were completely consumed as detected by ESI. The reaction was worked up by removing THF and washing the aqueous layer with Et2O twice. The pH of the aqueous layer was then adjusted to 1 using conc. HCl. The product was extracted with EtOAc and solvent removed in vacuo to provide the product as a white solid. The product was purified by crystallization from EtOAc to give 8.04 g (90%) of clear crystals of 27. ES MS [M−H]−232.1.

Workup

  1. customwere completely consumed
  2. customby removing THF
  3. washwashing the aqueous layer with Et2O twice
  4. extractionThe product was extracted with EtOAc and solvent
  5. customremoved in vacuo

Sources & evidence

ORD record
ord-b61dd1c778e4448399913a48018b4afe
Source dataset
uspto-grants-2007_08
Patent number
US07253180B2

Reaction notes

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