Diethylenetriaminepentaacetic acid → HCID 178419119, compound

HRID 1271525Notes

Reaction equation

HRID 1271525 reaction equation
[CH2:1]([N:12]([CH2:24][C:25]([OH:27])=[O:26])[CH2:13][CH2:14][N:15]([CH2:20][C:21]([OH:23])=[O:22])[CH2:16][C:17]([OH:19])=[O:18])[CH2:2][N:3]([CH2:8][C:9]([OH:11])=[O:10])[CH2:4][C:5]([OH:7])=[O:6].C(N(CC)CC)C.[BH:35]1[CH:40]2[CH2:41][CH2:42][CH2:43][CH:36]1[CH2:37][CH2:38][CH2:39]2.[NH2:44][C@H:45]([C:51]([OH:53])=[O:52])[CH2:46][CH2:47][CH2:48][CH2:49][NH2:50]>CC#N>[BH:35]1[CH:40]2[CH2:41][CH2:42][CH2:43][CH:36]1[CH2:37][CH2:38][CH2:39]2.[NH2:44][C@H:45]([C:51]([OH:53])=[O:52])[CH2:46][CH2:47][CH2:48][CH2:49][NH2:50].[CH2:13]([N:12]([CH2:24][C:25]([OH:27])=[O:26])[CH2:1][CH2:2][N:3]([CH2:4][C:5]([OH:7])=[O:6])[CH2:8][C:9]([OH:11])=[O:10])[CH2:14][N:15]([CH2:20][C:21]([OH:23])=[O:22])[CH2:16][C:17]([OH:19])=[O:18]

Participants

5

Reactant 3

HCID 3053Diethylenetriaminepentaacetic acidHCID 8471TriethylamineHCID 178419118HCID 178419118, compound

Product 1

HCID 178419119HCID 178419119, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Conditions

Temperature
55 °C

Procedure

A sample of DTPA (1 eq) is added to a solution of acetonitrile (CH3CN, 0.1 M), followed by the addition of triethylamine (NEt3) (5 eq) to provide a cloudy solution that is then degassed for 20 minutes before stirring at 55° C. for 1 hour. The resulting clear colorless solution is then cooled to −45° C., followed by the dropwise addition of isobutylchlorofomate (IBCF) (1.1 eq) and stirring for 1 hour at −45° C., resulting in a white slurry. The slurry is then added to a CH3CN solution of 9-BBN-lysine, 3, (1 eq), and the reaction mixture is stirred at ambient temperature for 12 hours. The volatiles are removed under reduced pressure and the residue recrystallized from THF/diethyl ether (Et2O) to provide the 9-BBN-lysine-DTPA, 4, product as a white solid.

Workup

  1. customto provide a cloudy solution that
  2. customis then degassed for 20 minutes
  3. temperatureThe resulting clear colorless solution is then cooled to −45° C.
  4. additionfollowed by the dropwise addition of isobutylchlorofomate (IBCF) (1.1 eq)
  5. stirringstirring for 1 hour at −45° C.
  6. customresulting in a white slurry
  7. stirringthe reaction mixture is stirred at ambient temperature for 12 hours
  8. customThe volatiles are removed under reduced pressure
  9. customthe residue recrystallized from THF/diethyl ether (Et2O)

Sources & evidence

ORD record
ord-0efae3ac95b2477a9aa464dd588055da
Source dataset
uspto-grants-2007_04
Patent number
US07205385B2

Reaction notes

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