Reaktion #57487

Reaktionsgleichung

(3R,3aS,6aR)hexahydrofuro[2,3-b]furan-3-yl (1S,2R)-1-benzyl-3-[{[4-(benzyloxy)phenyl]sulfonyl}(cyclohexyloxy)amino]-2-hydroxypropylcarbamate

→

(3R,3aS,6aR)hexahydrofuro[2,3-b]furan-3-yl (1S,2R)-1-benzyl-3-{(cyclohexyloxy)[(4-hydroxyphenyl)sulfonyl]amino}-2-hydroxypropylcarbamate

Ausbeute 87.1%

Lösungsmittel

ethyl acetate

Reaktionsbedingungen

Aufarbeitung

1. 1
   Filtrationthe reaction mixture was filtered
2. 2
   Sonstigeevaporated in vacuo to a residue
3. 3
   SonstigeThe residue was purified on a preparative TLC plate (20×20 cm, 500 μM)
4. 4
   Wascheneluting with 3:2 ethyl acetate
5. 5
   SonstigeThe product band was removed
6. 6
   Wascheneluted with 4:1 methylene chloride
7. 7
   Filtrationmethanol, filtered
8. 8
   Sonstigeevaporated in vacuo
9. 9
   SonstigeThe residue was triturated with water
10. 10
    Filtrationfiltered
11. 11
    Sonstigedried under high vacuum

Vorschrift

A solution of (3R,3aS,6aR)hexahydrofuro[2,3-b]furan-3-yl (1S,2R)-1-benzyl-3-[{[4-(benzyloxy)phenyl]sulfonyl}(cyclohexyloxy)amino]-2-hydroxypropylcarbamate (140 mg, 0.206 mmol) in ethyl acetate (5 mL) was combined with Palladium on carbon (10 wt %, 28 mg) and reduced under an atmosphere of Hydrogen gas. After stirring for 16 hours, the reaction mixture was filtered and evaporated in vacuo to a residue. The residue was purified on a preparative TLC plate (20×20 cm, 500 μM) eluting with 3:2 ethyl acetate:hexane. The product band was removed, eluted with 4:1 methylene chloride:methanol, filtered, and evaporated in vacuo. The residue was triturated with water, filtered and dried under high vacuum to provide (3R,3aS,6aR)hexahydrofuro[2,3-b]furan-3-yl (1S,2R)-1-benzyl-3-{(cyclohexyloxy)[(4-hydroxyphenyl)sulfonyl]amino}-2-hydroxypropylcarbamate (106 mg, 87%) as a white solid. H1-NMR (chloroform-D3): 1.27 (m, 6H), 1.67 (m, 5H), 2.05 (m, 2H), 2.93 (m, 4H), 3.11 (b, 1H), 3.68 (m, 2H), 3.90 (m, 4H), 4.19 (m, 1H), 4.81 (d, 1H), 4.99 (m, 1H), 5.65 (d, 1H), 6.24 (b, 1H), 6.92 (d, 2H), 7.22 (m, 5H), 7.67 (d, 2H). MS(ESI): 613(M+Na).

Quelle