Sodium Hydroxide → HCID 18913793, compound

HRID 1648169Notes

Reaction equation

HRID 1648169 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([CH2:10][CH2:11][N:12]2[CH2:23][CH2:22][N:21]([CH2:24][C:25]([O:27]CC)=[O:26])[CH2:20][CH2:19][N:18]([CH2:30][C:31]([O:33]CC)=[O:32])[CH2:17][CH2:16][N:15]([CH2:36][C:37]([O:39]CC)=[O:38])[CH2:14][CH2:13]2)=[CH:6][CH:5]=1)([O-:3])=[O:2].[OH-].[Na+]>O>[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([CH2:10][CH2:11][N:12]2[CH2:13][CH2:14][N:15]([CH2:36][C:37]([OH:39])=[O:38])[CH2:16][CH2:17][N:18]([CH2:30][C:31]([OH:33])=[O:32])[CH2:19][CH2:20][N:21]([CH2:24][C:25]([OH:27])=[O:26])[CH2:22][CH2:23]2)=[CH:6][CH:5]=1)([O-:3])=[O:2]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 86748807HCID 86748807, compound

Product 1

HCID 18913793HCID 18913793, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

To a suspension of 200 mg (0.35 mmole) of 1-[2-(4-nitrophenyl)ethyl]-1,4,7,10-tetraazacyclododecane-4,7,10-triacetic acid, triethyl ester (prepared by the procedure of Example 19) in 15 ml of water was added 59 μl of NaOH (50% wt/wt, 3 eq). The mixture was stirred at 80° C. for 6 hours. The resulting homogeneous orange solution was then cooled to room temperature and freeze-dried to yield a brown solid which was purified by HPLC (Q-Sepharose™, HPLC System III) using a linear gradient of 0-10% aqueous HOAc over 60 minutes to yield (50%) of the hydrolyzed product 1-[2-(4-nitrophenyl)ethyl]-1,4,7,10-tetraazacyclododecane-4,7,10-triactic acid, and characterized by:

Workup

  1. temperatureThe resulting homogeneous orange solution was then cooled to room temperature
  2. customfreeze-dried
  3. customto yield a brown solid which
  4. customwas purified by HPLC (Q-Sepharose™, HPLC System III)
  5. customover 60 minutes

Sources & evidence

ORD record
ord-db2b8435a10745219db9214395ff545e
Source dataset
uspto-grants-1995_07
Patent number
US05435990

Reaction notes

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