ChemicalBook CAS DataBase List hexadecanedioic acid tert-butyl ester N-hydroxysuccinimide ester

hexadecanedioic acid tert-butyl ester N-hydroxysuccinimide ester synthesis

5synthesis methods

Product Name:hexadecanedioic acid tert-butyl ester N-hydroxysuccinimide ester
CAS Number:843666-28-4
Molecular formula:C24H41NO6
Molecular Weight:439.59

843666-27-3 Synthesis

16-(Tert-butoxy)-16-oxohexadecanoic acid

843666-27-3
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105832-38-0
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hexadecanedioic acid tert-butyl ester N-hydroxysuccinimide ester

843666-28-4
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Yield:843666-28-4 79%

Reaction Conditions:

with N-ethyl-N,N-diisopropylamine in tetrahydrofuran;

Steps:

1.2

The mono tert-butyl ester (2 g, 5.8 mmol) was dissolved in THF (20 ml) and treated with TSTU (2.1 g, 7.0 mmol) and DIEA (1.2 ml, 7.0 mmol) and stirred overnight. The mixture was filtered, and the filtrate was evaporated in vacuo. The residue was dissolved in AcOEt and washed twice with cold 0.1 M HCI and water. Drying over MgSO₄ and evaporation in vacuo gave succinimidyl tert-butyl hexadecandioate, 2.02 g (79%).¹H-NMR (CDCI₃) δ: 2.84 (s, 4H), 2.60 (t, 2H), 2.20 (t, 2H), 1.74 (p, 2H), 1.56 (m, 2H), 1.44 (s, 9H), 1.40 (m, 2H), 1.30-1.20 (m, 18H).

References:

WO2007/128817,2007,A2 Location in patent:Page/Page column 81-82

6066-82-6 Synthesis