Reaktion #57474

Reaktionsgleichung

(3R,3aS,6aR)hexahydrofuro[2,3-b]furan-3-yl N-((1S,2R)-1-benzyl-3-(cyclopentyloxy)[(3-hydroxyphenyl)sulfonyl]amino-2-hydroxypropyl)carbamate

2-bromopropane

potassium carbonate

→

white solid

Ausbeute 48.0%

(3R,3aS,6aR)hexahydrofuro[2,3-b]furan-3-yl N-((1S,2R)-1-benzyl-3-(cyclopentyloxy)[(3-isopropoxyphenyl)sulfonyl]amino-2-hydroxypropyl)carbamate

Ausbeute 48.0%

Lösungsmittel

DMF

Reaktionsbedingungen

Aufarbeitung

1. 1
   EinengenThe reaction mixture was concentrated under vacuum to a residue
2. 2
   workup.ADDITIONdiluted with ethyl acetate (2 mL)
3. 3
   WaschenThe reaction was washed in distilled water
4. 4
   Trocknenbrine, and was dried over magnesium sulfate
5. 5
   EinengenThe dried solution was then concentrated to an oil
6. 6
   Sonstigepurified by silica gel chromatography (2:1 hexanes/ethyl acetate)

Vorschrift

(3R,3aS,6aR)hexahydrofuro[2,3-b]furan-3-yl N-((1S,2R)-1-benzyl-3-(cyclopentyloxy)[(3-hydroxyphenyl)sulfonyl]amino-2-hydroxypropyl)carbamate (0.13 mmol, 75 mg) was combined with 2-bromopropane (0.26 mmol, 0.025 mL), potassium carbonate (0.65 mmol, 90 mg), tetrabutylammonium iodide (5 mg) and anhydrous DMF (1 mL). The reaction was stirred under a nitrogen atmosphere at room temperature for 72 hours. The reaction mixture was concentrated under vacuum to a residue and diluted with ethyl acetate (2 mL). The reaction was washed in distilled water and brine, and was dried over magnesium sulfate. The dried solution was then concentrated to an oil and purified by silica gel chromatography (2:1 hexanes/ethyl acetate) to yield 38 mg (48%) of a white solid. Rf=0.40 (2:1 hexanes/ethyl acetate); H1-NMR (CDCl3): δ 7.40 (1H,m), 7.33-7.10 (9H,m), 5.63 (1H,s), 5.00 (1H,m), 4.80 (2H,m), 4.58 (1H,m), 3.88 (4H,m), 3.67 (2H,m), 3.13 (1H,br.s), 3.00 (2H,m), 2.94-2.74 (2H,m), 1.88-1.71 (5H,m), 1.69-1.43 (5H,m), 1.35 (6H,d).

Quelle