Ethyl bromoacetate → Diethylenetriaminepentaacetic acid

HRID 1661515Notes

Reaction equation

HRID 1661515 reaction equation
[NH2:1][CH2:2][CH2:3][NH:4][CH2:5][CH2:6][NH2:7].F[C:9](F)(F)[C:10]([O:12]CC)=[O:11].C([O:19][C:20](=[O:23])[CH2:21]Br)C.[H-].[Na+]>>[CH2:3]([N:4]([CH2:9][C:10]([OH:12])=[O:11])[CH2:5][CH2:6][N:7]([CH2:21][C:20]([OH:19])=[O:23])[CH2:9][C:10]([OH:12])=[O:11])[CH2:2][N:1]([CH2:9][C:10]([OH:12])=[O:11])[CH2:9][C:10]([OH:12])=[O:11]

Participants

5

Reactant 4

HCID 7748Ethyl bromoacetateHCID 8111DiethylenetriamineHCID 9794Ethyl trifluoroacetateHCID 24758Sodium hydride

Product 1

HCID 3053Diethylenetriaminepentaacetic acid

Procedure

Various esters of DTPA were prepared from diethylenetriamine, 6. The primary amines could be selectively protected as the di-trifluoroacetamide by reaction with ethyl trifluoroacetate to produce 9 in good yield. Reaction of 9 with 3 equivalents of ethylbromoacetate and NaH produced the triester 10. Reaction of 9 with 1 equivalent of ethylbromoacetate produced the monoester 11.

Workup

  1. customto produce 9 in good yield

Sources & evidence

ORD record
ord-cbc8fac7932c4470b56ef38e6be86d25
Source dataset
uspto-grants-2011_10
Patent number
US08030358B2

Reaction notes

Loading…