Hydrochloric Acid → HCID 15702830, compound

HRID 2259544Notes

Reaction equation

HRID 2259544 reaction equation
[C:1]([CH2:4][N:5]1[CH2:16][CH2:15][NH:14][CH2:13][CH2:12][N:11]([CH2:17][C:18]([OH:20])=[O:19])[CH2:10][CH2:9][N:8]([CH2:21][C:22]([OH:24])=[O:23])[CH2:7][CH2:6]1)([OH:3])=[O:2].[C:25](=O)([O-])[O-].[K+].[K+].CI.Cl.CO.CC(C)=O>CO>[CH3:25][N:14]1[CH2:13][CH2:12][N:11]([CH2:17][C:18]([OH:20])=[O:19])[CH2:10][CH2:9][N:8]([CH2:21][C:22]([OH:24])=[O:23])[CH2:7][CH2:6][N:5]([CH2:4][C:1]([OH:3])=[O:2])[CH2:16][CH2:15]1

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 6328Methyl iodide2×HCID 11430Potassium CarbonateHCID 1078301,4,7-Tris(carboxymethyl)-1,4,7,10-tetraazacyclododecaneHCID 21894497Aceton-methanol

Product 1

HCID 15702830HCID 15702830, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 250 mg (0.723 mmol) of 1,4,7-triscarboxymethyl-1,4,7,10-tetraazacyclododecane in 2.9 ml of methanol was added 220 mg (1.59 mmol) of potassium carbonate. To the resulting mixture was added 308 mg (2.17 mmol, 3 equiv) of methyl iodide. Within a short time, most of the solids dissolved. After 15 hours at 21° C., a mass of crystals had separated. Additional methanol was added (2 ml) to dissolve the solid. After 23 hours, an additional 102 mg (0.72 mmol) of methyl iodide was added. After an additional 16 hours, the solution was acidified with concentrated hydrochloric acid and the volatiles were removed on the rotary evaporator. The residue was extracted with methanol, filtered, and the methanol evaporated. The residue was crystallized twice from methanol/acetone yielding 56 mg (0.16 mmol) of a colorless solid, melting point 215°-240° (dec.). 13C NMR (D2O, ppm vs TMS): 177.2, 171.1, 57.2, 56.5, 54.1, 52.6, 50.1, 49.9, 43.7. Mass spectrum (FAB): m/e 359 (M-H) and 361 (M+H).

Workup

  1. dissolutionWithin a short time, most of the solids dissolved
  2. customa mass of crystals had separated
  3. additionAdditional methanol was added (2 ml)
  4. dissolutionto dissolve the solid
  5. waitAfter 23 hours
  6. waitAfter an additional 16 hours
  7. customthe volatiles were removed on the rotary evaporator
  8. extractionThe residue was extracted with methanol
  9. filtrationfiltered
  10. customthe methanol evaporated

Sources & evidence

ORD record
ord-8db36073585f449b9f90aed0a77e910f
Source dataset
uspto-grants-1995_12
Patent number
US05474756

Reaction notes

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