Hydrochloric Acid → DO2A

HRID 1601641Notes

Reaction equation

HRID 1601641 reaction equation
[O:1]=[C:2]1[N:13]2[CH2:14][CH2:15][N:4]([CH2:5][CH2:6][NH:7][CH2:8][CH2:9][N:10]([CH2:16][C:17]([OH:19])=[O:18])[CH2:11][CH2:12]2)[CH2:3]1.Cl.[OH-:21].[Na+]>>[N:10]1([CH2:16][C:17]([OH:19])=[O:18])[CH2:11][CH2:12][NH:13][CH2:14][CH2:15][N:4]([CH2:3][C:2]([OH:21])=[O:1])[CH2:5][CH2:6][NH:7][CH2:8][CH2:9]1

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 22117785HCID 22117785, compound

Product 1

HCID 387353DO2AYield 86.5%

Procedure

20 g (0.074 mol) of 12-oxo-1,4,7,10-tetraazabicyclo[8.2.2]tetradecane-4-acetic acid, prepared as described in example 5, are dissolved in 88.8 g of 10% NaOH. The solution is refluxed overnight, then cooled and acidified to pH 12 by addition of conc. HCl. The resulting solution is percolated on a column containing 600 ml of anionic exchanger resin IRA420 (Rohm & Haas), which is washed repeatedly with water, then eluted with 1N HCl. The fractions containing the product are combined and concentrated at reduced pressure to a volume of about 500 mL. The solution is percolated on a column containing 2 L of polyvinylpyridine resin (PVP), eluting with water, the fractions containing the desalted product are collected, combined and concentrated to dryness under vacuum. The crude solid is recrystallized from methanol/acetone=8/2, finally dried in a static drier at 50° C. under vacuum. 18.5 g (0.064 mol) of 1,4,7,10-tetraazacyclododecane-1,7-diacetic acid are obtained.

Workup

  1. temperatureThe solution is refluxed overnight
  2. temperaturecooled
  3. washis washed repeatedly with water
  4. washeluted with 1N HCl
  5. additionThe fractions containing the product
  6. concentrationconcentrated at reduced pressure to a volume of about 500 mL
  7. additioncontaining 2 L of polyvinylpyridine resin (PVP)
  8. washeluting with water
  9. additionthe fractions containing the desalted product
  10. customare collected
  11. concentrationconcentrated to dryness under vacuum
  12. customThe crude solid is recrystallized from methanol/acetone=8/2
  13. customfinally dried in a static drier at 50° C. under vacuum

Sources & evidence

ORD record
ord-9a5a405bd9dc470a84a75bff67f4e636
Source dataset
uspto-grants-1999_11
Patent number
US05977353

Reaction notes

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