Hydrochloric Acid → 1,4,7-Tris(carboxymethyl)-1,4,7,10-tetraazacyclododecane

HRID 1422428

Reaction equation

HRID 1422428 reaction equation
NCC(O)CO.Cl.[C:8]([CH:11]([N:18]1[CH2:29][CH2:28][N:27]([CH:30]([C:37]([OH:39])=[O:38])CCCC(O)=O)[CH2:26][CH2:25][NH:24][CH2:23][CH2:22][N:21]([CH:40](CCCC)[C:41]([OH:43])=[O:42])[CH2:20][CH2:19]1)CCCC(O)=O)([OH:10])=[O:9].C1C(=O)N(O)C(=O)C1S([O-])(=O)=O.[Na+].CCN=C=NCCCN(C)C.[OH-].[Na+]>O>[CH2:25]1[NH:24][CH2:23][CH2:22][N:21]([CH2:40][C:41]([OH:43])=[O:42])[CH2:20][CH2:19][N:18]([CH2:11][C:8]([OH:10])=[O:9])[CH2:29][CH2:28][N:27]([CH2:30][C:37]([OH:39])=[O:38])[CH2:26]1

Participants

8

Reactant 6

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 735613-Amino-1,2-propanediolHCID 3520574n-hydroxysulfosuccinimide sodium saltHCID 667390892-[4,7-Bis(1,4-dicarboxybutyl]-1,4,7,10-tetraazacyclododec-1-yl]hexanoic acid

Product 1

HCID 1078301,4,7-Tris(carboxymethyl)-1,4,7,10-tetraazacyclododecane

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution containing 0.26 mg of 3-aminopropane-1,2-diol in 6 μl of water is prepared. The pH is adjusted to 6 with HCl. 0.5 mg of gallium complex of 2-[4,7-bis(1,4-dicarboxybutyl]-1,4,7,10-tetraazacyclododec-1-yl]hexanoic acid are added to the above solution. The pH is again adjusted before adding 0.071 mg of sulfo-NHS and 0.062 mg of EDCI. The pH is checked and adjusted to 6 with 2N NaOH. After an overnight period at AT, the reaction medium is concentrated to approximately 2 ml and then precipitated from 10 ml of ethanol. The solid is filtered off, washed with ethanol and diethyl ether, and then purified on silanized silica RP2, elution being carried out with water only. 0.2 mg of product is obtained.

Workup

  1. customis prepared
  2. concentrationthe reaction medium is concentrated to approximately 2 ml
  3. customprecipitated from 10 ml of ethanol
  4. filtrationThe solid is filtered off
  5. washwashed with ethanol and diethyl ether
  6. custompurified on silanized silica RP2, elution

Sources & evidence

ORD record
ord-367de10a3cab4b43a995523b367e5bc6
Source dataset
uspto-grants-2015_01
Patent number
US08926945B2

Linked notes

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