Hydrochloric Acid → HCID 86747543, compound

HRID 1757772Notes

Reaction equation

HRID 1757772 reaction equation
CC([O:5]C(=O)[NH:7][CH2:8][CH2:9][NH:10][C:11](=[O:46])[CH2:12][N:13]([CH2:42][C:43]([OH:45])=[O:44])[CH2:14][CH2:15][N:16]([CH2:38][C:39]([OH:41])=[O:40])[CH2:17][CH2:18][N:19]([CH2:34][C:35]([OH:37])=[O:36])[CH2:20][C:21](=[O:33])[NH:22][CH2:23][CH2:24][NH:25]C(OC(C)(C)C)=O)(C)C.Cl.[OH-:49].[Na+]>O>[OH2:5].[OH2:49].[NH2:25][CH2:24][CH2:23][NH:22][C:21](=[O:33])[CH2:20][N:19]([CH2:34][C:35]([OH:37])=[O:36])[CH2:18][CH2:17][N:16]([CH2:38][C:39]([OH:41])=[O:40])[CH2:15][CH2:14][N:13]([CH2:12][C:11]([NH:10][CH2:9][CH2:8][NH2:7])=[O:46])[CH2:42][C:43]([OH:45])=[O:44]

Participants

5

Reactant 3

HCID 313Hydrochloric Acid2×HCID 14798Sodium HydroxideHCID 19103128HCID 19103128, compound

Product 1

HCID 86747543HCID 86747543, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

The DTPA-B(tBA)EA prepared above was dissolved in 110 mL DI water, adjustedto pH 7 (5N HCl), and cooled in an ice bath. To the cool stirred solution was added concentrated HCl (39 mL) in one portion. The mixture was stirred10 minutes in the ice bath then for 2 hours at ambient temperature. The solution was then cooled in an ice bath, titrated to pH 7 (50% NaOH), and concentrated by rotary evaporation to a dry solid (50 g). A portion of solid NaCl was removed from this material by suspending the solid in 50 mLDI water and vacuum filtering through a medium fritted glass funnel. The filtrate was adjusted to pH 2.5 (5N HCl), concentrated to a 50 mL suspension, and vacuum filtered through a coarse fritted glass funnel to remove additional solid NaCl. The filtrate was loaded onto a 9.5×2.0" (24.1×5.1 cm) column bed of Bio-Rad AG50-X8 (H+,200-400 mesh). The column was eluted under nitrogen pressure with 0.75 L DIwater followed by 1.25 L of 2N ammonium hydroxide. The product eluted with 2N ammonium hydroxide. The UV active fraction was concentrated by rotary evaporation to an oily residue. The residue was dissolved in 100 mL 1N acetic acid, concentrated by rotary evaporation, reconcentrated repeatedlyfrom water (13×100 mL) to remove ammonium acetate, and lyophilized (10μ, 14 hours) to afford DTPA-B(AE)A.2H2O. 1H NMR (250 MHz, D2O/DCl:pH 2.3): δ 2.95 (t, 4H, J=5.7 Hz), δ 3.09-3.28 (b, 8H), δ 3.35 (t, 4H, J=5.7 Hz), δ 3.51 (s, 4H), δ 3.55 (s, 2H), δ 3.66 (s, 4H).

Workup

  1. temperaturecooled in an ice bath
  2. temperatureThe solution was then cooled in an ice bath
  3. concentrationconcentrated by rotary evaporation to a dry solid (50 g)
  4. customA portion of solid NaCl was removed from this material
  5. filtrationfiltering through a medium fritted glass funnel
  6. concentrationconcentrated to a 50 mL suspension, and vacuum
  7. filtrationfiltered through a coarse fritted glass funnel
  8. customto remove additional solid NaCl
  9. washThe column was eluted under nitrogen pressure with 0.75 L DIwater
  10. washThe product eluted with 2N ammonium hydroxide
  11. concentrationThe UV active fraction was concentrated by rotary evaporation to an oily residue
  12. dissolutionThe residue was dissolved in 100 mL 1N acetic acid
  13. concentrationconcentrated by rotary evaporation
  14. customto remove ammonium acetate
  15. custom(10μ, 14 hours)

Sources & evidence

ORD record
ord-9a97aef677bd46acbb0210021b1c204b
Source dataset
uspto-grants-1995_08
Patent number
US05446145

Reaction notes

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