Reaktion #40606

Reaktionsgleichung

39

(2S,4aR,6aR,7R,9S,10aS,10bR)-9-(Amino)-2-(3-furanyl)-dodecahydro-6a,10b-dimethyl-4,10-dioxo-2H-naphtho[2,1-c]pyran-7-carboxylic acid methyl ester

benzenesulfonyl chloride

triethylamine

MeOH

→

43

Ausbeute 98.9%

(2S,4aR,6aR,7R,9S,10aS,10bR)-9-(Benzenesulfonylamino)-2-(3-furanyl)-dodecahydro-6a,10b-dimethyl-4,10-dioxo-2H-naphtho[2,1-c]pyran-7-carboxylic acid methyl ester

Ausbeute 98.9%

Lösungsmittel

CH2Cl2

Reaktionsbedingungen

Aufarbeitung

1. 1
   Waschenthe solution was washed with 10% HCl (3×25 mL) and saturated NaCl (2×25 mL)
2. 2
   Trocknendried (Na2SO4)
3. 3
   Filtrationfiltered
4. 4
   Einengenconcentrated under reduced pressure
5. 5
   Sonstigeto yield a crude solid
6. 6
   SonstigeThe solid was purified by flash column chromatography (eluent: n-hexanes/EtOAc, 1:1)
7. 7
   SonstigeRemoval of the solvent under reduced pressure

Vorschrift

A solution of 39 (0.08 g, 0.21 mmol), benzenesulfonyl chloride (0.07 g, 0.42 mmol), triethylamine (0.06 g, 0.63 mmol), and a catalytic amount of DMAP in CH2Cl2 (40 mL) was stirred at room temperature for 18 h. Absolute MeOH was then added and the solution was washed with 10% HCl (3×25 mL) and saturated NaCl (2×25 mL), dried (Na2SO4), filtered, and concentrated under reduced pressure to yield a crude solid. The solid was purified by flash column chromatography (eluent: n-hexanes/EtOAc, 1:1). Removal of the solvent under reduced pressure gave 0.11 g (97%) of 43 as a white solid, mp 271-273° C. (EtOAc/n-hexanes): 1H NMR (acetone-d6): δ 0.98 (3H, s); 1.29 (3H, s); 1.52 (2H, m); 1.65 (1H, m); 1.70 (1H, ddd, J=3.0, 3.0, 12.6); 1.82 (1H, ddd, J=1.8, 5.1, 13.5); 1.95 (1H, ddd, J=6.3, 6.3, 10.2); 2.09 (1H, d, J=13.2); 2.22 (1H, dd, J=2.7, 11.7); 2.29 (1H, ddd, J=3.3, 6.9, 13.5); 2.62 (1H, s); 2.96 (1H, dd, J=3.5, 13.4); 3.66 (3H, s); 4.19 (1H, m); 5.47 (1H, dd, J=5.4, 12.0); 6.53 (1H, dd, J=0.9, 1.5); 6.69 (1H, d, J=8.4); 7.38 (1H, m); 7.40 (1H, d, J=6.9); 7.44 (1H, dd, J=2.1, 3.0); 7.60 (2H, m); 7.80 (2H, m); 13C NMR (acetone-d6): δ 15.7, 16.8, 19.4, 35.5, 36.4, 39.1, 43.4, 44.3, 51.5, 52.2, 54.8, 61.2, 64.7, 72.4, 110.0, 127.5, 128.2, 130.1, 133.5, 141.2, 142.4, 145.1, 171.7, 173.0, 205.3.

Quelle