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

HRID 2264100Notes

Reaction equation

HRID 2264100 reaction equation
[CH2:1]1[N:12](CC(O)=O)[CH2:11][CH2:10][N:9]([CH2:17][C:18]([OH:20])=[O:19])[CH2:8][CH2:7][N:6]([CH2:21][C:22]([OH:24])=[O:23])[CH2:5][CH2:4][N:3]([CH2:25][C:26]([OH:28])=[O:27])[CH2:2]1.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C>CN1C(=O)CCC1>[CH2:11]1[NH:12][CH2:1][CH2:2][N:3]([CH2:25][C:26]([OH:28])=[O:27])[CH2:4][CH2:5][N:6]([CH2:21][C:22]([OH:24])=[O:23])[CH2:7][CH2:8][N:9]([CH2:17][C:18]([OH:20])=[O:19])[CH2:10]1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 121841DotaHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)

Product 1

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

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

8.0 equivalents of DOTA mono acid was dissolved in NMP and treated with 8.0 equivalents of HBTU and 16.0 equivalents of DIEA. This solution was stirred for 15 min at RT and then transferred to the amine on the resin and the coupling was continued for 24 h at RT. The resin was then drained, washed and then the peptide was cleaved and purified.

Workup

  1. waitthe coupling was continued for 24 h at RT
  2. washwashed
  3. custompurified

Sources & evidence

ORD record
ord-0da1712c0f1b43bea9f9891c304ba261
Source dataset
uspto-grants-2010_12
Patent number
US07850947B2

Reaction notes

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