Reaktion #649708

Reaktionsgleichung

hexadecandioic acid mono t-butyl ester

HOAt

DCC

5-Amino-isophthalic acid mono t-butyl ester

DIPEA

→

title compound

Ausbeute 86.0%

5-(15-tert-Butoxycarbonyl-pentadecanoylamino)-isophthalic acid mono-tert-butyl ester

Ausbeute 86.0%

Lösungsmittel

DCM

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe oil bath was removed
2. 2
   workup.STIRRINGThe mixture was stirred at RT over night under nitrogen
3. 3
   FiltrationThe yellow suspension was filtered
4. 4
   Einengenthe filtrate was concentrated
5. 5
   workup.DISSOLUTIONThe residue was redissolved in EtOAc
6. 6
   Extraktionextracted with 0.1 N HCl (2×), brine (1×)
7. 7
   Trocknendried (Na2SO4)
8. 8
   Einengenconcentrated
9. 9
   Sonstigeto give a white solid, which
10. 10
    Sonstigewas purified twice by flash chromatography

Vorschrift

To a solution of hexadecandioic acid mono t-butyl ester (100 mg, 0.29 mmol) in dry DCM (2 ml), HOAt (44 mg, 0.29 mmol) and DCC (72 mg, 32 mmol) was added. The mixture was stirred at 50° C. for 1 h. The oil bath was removed. 5-Amino-isophthalic acid mono t-butyl ester (69 mg, 0.29) and DIPEA (0.07 ml, 0.32 mmol) was added. The mixture was stirred at RT over night under nitrogen. The yellow suspension was filtered and the filtrate was concentrated. The residue was redissolved in EtOAc and extracted with 0.1 N HCl (2×), brine (1×), dried (Na2SO4) and concentrated to give a white solid, which was purified twice by flash chromatography using EtOAc/Hept 1:2+5% AcOH. The title compound was obtained in 86% yield (0.140 g) as an oil containing an impurity.

Quelle