ChemicalBook CAS DataBase List 1,4,7,10-Tetraazacyclododecane-1,4,7-triacetic acid, 10-[2-[[2-(2,5-dihydro-2,5-dioxo-1H-pyrrol-1-yl)ethyl]amino]-2-oxoethyl]-, 1,4,7-tris(1,1-dimethylethyl) ester

1,4,7,10-Tetraazacyclododecane-1,4,7-triacetic acid, 10-[2-[[2-(2,5-dihydro-2,5-dioxo-1H-pyrrol-1-yl)ethyl]amino]-2-oxoethyl]-, 1,4,7-tris(1,1-dimethylethyl) ester synthesis

5synthesis methods

Product Name:1,4,7,10-Tetraazacyclododecane-1,4,7-triacetic acid, 10-[2-[[2-(2,5-dihydro-2,5-dioxo-1H-pyrrol-1-yl)ethyl]amino]-2-oxoethyl]-, 1,4,7-tris(1,1-dimethylethyl) ester
CAS Number:1613382-10-7
Molecular formula:C34H58N6O9
Molecular Weight:694.86

125923-10-6
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TRI-TERT-BUTYL 1 4 7 10-TETRAAZACYCLODOD

137076-54-1
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$22.00/100mg

1,4,7,10-Tetraazacyclododecane-1,4,7-triacetic acid, 10-[2-[[2-(2,5-dihydro-2,5-dioxo-1H-pyrrol-1-yl)ethyl]amino]-2-oxoethyl]-, 1,4,7-tris(1,1-dimethylethyl) ester

1613382-10-7
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Yield:1613382-10-7 57%

Reaction Conditions:

with N-ethyl-N,N-diisopropylamine;HATU in N,N-dimethyl-formamide at 20;Inert atmosphere;

Steps:

4 Example 4- Synthesis of tri-tert-butyl 2,2',2'-(10-(2-((2-(2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)ethyl)amino)-2-oxoethyl)-1,4,7,10-tetraazacyclododecane-1,4,7-triyl)triacetate

Example 4- Synthesis of tri-tert-butyl 2,2',2'-(10-(2-((2-(2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)ethyl)amino)-2-oxoethyl)-1,4,7,10-tetraazacyclododecane-1,4,7-triyl)triacetate
To a solution of product 2-(4,7,10-Tris(2-(tert-butoxy)-2-oxoethyl)-1,4,7,10-tetraazacyclododecan-1-yl)acetic acid (572.7 mg, 1 mmol) in dry DMF (15 mL), amino-maleimide 137 (483.3 mg, 1 mmol) was added with HATU (272 mg, 1.4 mmol) and DIPEA (360 μL, 1.84 mmol).
The mixture was stirred overnight at room temperature.
After removing the solvent under the vacuum, the crude product was purified by flash chromatography on silica gel (CH₂Cl₂/MeOH, 90:10) to give compound tri-tert-butyl 2,2',2'-(10-(2-((2-(2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)ethyl)amino)-2-oxoethyl)-1,4,7,10-tetraazacyclododecane-1,4,7-triyl)triacetate as a white foam (396 mg, 57 %).
Rf : 0.3 (CH₂Cl₂/MeOH, 90:10).
1H NMR (300MHz, CDCl3) δ 8.30 (b, 1H, NH), 6.86 (s,2H, H6'), 3.78-3.54 (br, 4H, H3', H4'), 3.54 (br, 4H, H13, H1'), 3.48 (br, 4H, H8), 3.09-2.99 (m, 8H, H2, H3), 2.97-2.86 (m, 8H, H5, H6), 1.46 (s, 18H, H12), 1.45 (s, 9H, H17).
13C NMR (75MHz, CDCl3) δ 171.6 (C2'), 171.0 (C5'), 170.4 (C9, C14), 134.2 (C6'), 81.5 (C16), 81.3 (C11), 57.8 (C1'), 55.7-55.2 (C8, C13), 54.1-51.5 (C2, C3), 51.0-48.9 (C5, C6), 38.0 (C4'), 32.7 (C3'), 27.8 (C17), 27.6 (C12).
MS (ESI) : m/z 695 [M + H]+.

References:

EP2740491,2014,A1 Location in patent:Paragraph 0131; 0132