Reaktion #617325

Reaktionsgleichung

(S)-4-(((9H-fluoren-9-yl)methoxy)carbonylamino)-5-tert-butoxy-5-oxopentanoic acid

tert-butyl 2-(2-(2-(2-aminoethoxy)ethoxy)ethoxy)ethylcarbamate

N,N-diisopropylethylamine

N,N,N′,N′-tetramethyl-O-(1H-benzotriazol-1-yl)uroniumhexafluorophosphate

→

(S)-tert-butyl 1-(9H-fluoren-9-yl)-24,24-dimethyl-3,8,22-trioxo-2,12,15,18,23-pentaoxa-4,9,21-triazapentacosane-5-carboxylate

Ausbeute 99.0%

Lösungsmittel

THF

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeAfter this time, the reaction was dry
2. 2
   Sonstigepurified by silica gel column chromatography
3. 3
   Wascheneluting with hexanes to ethyl acetate

Vorschrift

To (S)-4-(((9H-fluoren-9-yl)methoxy)carbonylamino)-5-tert-butoxy-5-oxopentanoic acid (721 mg, 1.69 mmol), tert-butyl 2-(2-(2-(2-aminoethoxy)ethoxy)ethoxy)ethylcarbamate (595 mg, 2.04 mmol), and N,N-diisopropylethylamine (0.9 mL, 5.2 mmol) in THF (20 mL), N,N,N′,N′-tetramethyl-O-(1H-benzotriazol-1-yl)uroniumhexafluorophosphate (1.29 g, 3.40 mmol) was added in one portion. The reaction was stirred at ambient temperature for 16 hours. After this time, the reaction was dry loaded onto silica and purified by silica gel column chromatography eluting with hexanes to ethyl acetate to afford (S)-tert-butyl 1-(9H-fluoren-9-yl)-24,24-dimethyl-3,8,22-trioxo-2,12,15,18,23-pentaoxa-4,9,21-triazapentacosane-5-carboxylate (1.17 g, 99%) as an off-white solid: 1H NMR (300 MHz, CDCl3) δ 7.77 (d, J=7.5 Hz, 2H), 7.62-7.59 (m, 2H), 7.44-7.38 (m, 2H), 7.36-7.26 (m, 2H), 6.78 (bs, 1H), 6.07 (bs, 2H), 5.77 (bs, 1H), 4.42-4.38 (m, 2H), 4.27-4.17 (m, 2H), 3.80-3.70 (m, 2H), 3.68-3.46 (m, 9H), 3.31-3.12 (m, 4H), 2.37-2.13 (m, 3H), 2.00-1.87 (m, 1H), 1.47 (s, 9H), 1.45 (s, 9H); ESI MS m/z=700 [M+H]+.

Quelle