Reaktion #1010721

Reaktionsgleichung

TFA

4-(octyloxy)benzoic acid

oxalyl chloride

tert-butyl 2-(N-(4-hydroxybenzyl)-4-(2-(4-methoxyphenyl)acetamido)benzamido)acetate

→

2-(4-(2-(4-methoxyphenyl)acetamido)-N-(4-((4-(octyloxy)benzoyl)oxy)benzyl)benzamido)acetic acid

Ausbeute 14.0%

Lösungsmittel

DCM

DCM

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigePrepared
2. 2
   workup.STIRRINGThe reaction was stirred at room temperature for 2 h
3. 3
   workup.STIRRINGAfter stirring for 2 h
4. 4
   Einengenthe solvent was concentrated
5. 5
   Sonstigethe product was purified by preparative HPLC

Vorschrift

Prepared using General Procedures 2 and 8: To a stirring solution of 4-(octyloxy)benzoic acid (30 mg, 0.119 mmol) in DCM (0.5 mL) were added DMF (1 drop) and oxalyl chloride (0.011 mL, 0.127 mmol). The reaction mixture was stirred at room temperature for 30 min. To this mixture was added a solution of tert-butyl 2-(N-(4-hydroxybenzyl)-4-(2-(4-methoxyphenyl)acetamido)benzamido)acetate INT-7 (40 mg, 0.079 mmol) and TEA (0.022 mL, 0.159 mmol) in DCM (1 mL). The reaction was stirred at room temperature for 2 h then TFA (1 mL) was added. After stirring for 2 h, the solvent was concentrated and the product was purified by preparative HPLC to afford 7.6 mg (14%) of 2-(4-(2-(4-methoxyphenyl)acetamido)-N-(4-((4-(octyloxy)benzoyl)oxy)benzyl)benzamido)acetic acid 17. LCMS-ESI (m/z) calculated for C40H44N2O8: 680; found 679 [M−H]−, tR=9.96 min (Method 4).

Quelle