تفاعل #57473

معادلة التفاعل

(3R,3aS,6aR)hexahydrofuro[2,3-b]furan-3-yl N-((1S,2R)-1-benzyl-3-(cyclopentyloxy)[(4-hydroxyphenyl)sulfonyl]amino-2-hydroxypropyl)carbamate

2-bromopropane

potassium carbonate

→

white solid

المردود 76.0%

(3R,3aS,6aR)hexahydrofuro[2,3-b]furan-3-yl N-((1S,2R)-1-benzyl-3-(cyclopentyloxy)[(4-isopropoxyphenyl)sulfonyl]amino-2-hydroxypropyl)carbamate

المردود 76.0%

المذيبات

DMF

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةwas heated to 50° C. for 3 hours
2. 2
   تركيزThe reaction mixture was concentrated under vacuum to a residue
3. 3
   workup.ADDITIONdiluted with ethyl acetate (2 mL)
4. 4
   غسيلThe reaction was washed in distilled water
5. 5
   تجفيفbrine, and was dried over magnesium sulfate
6. 6
   تركيزThe dried solution was then concentrated to an oil
7. 7
   أخرىpurified by silica gel chromatography (2:1 hexanes/ethyl acetate)

الإجراء التجريبي

(3R,3aS,6aR)hexahydrofuro[2,3-b]furan-3-yl N-((1S,2R)-1-benzyl-3-(cyclopentyloxy)[(4-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 stirred under a nitrogen atmosphere at room temperature for 15 hours, then was heated to 50° C. for 3 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 61 mg (76%) of a white solid. Rf=0.50 (2:1 hexanes/ethyl acetate); H1-NMR (CDCl3): δ 7.69 (2H,d), 7.33-7.13 (6H,m), 6.96 (2H,d), 5.65 (1H,s), 5.02 (1H,m), 4.86 (1H,m), 4.80 (1H,m), 4.65 (1H,m), 3.99-3.80 (5H,m), 3.69 (2H,m), 3.11 (1H,br.s), 3.09-2.98 (3H,m), 2.91 (1H,m), 2.83 (1H,m), 1.89-1.72 (4H,m), 1.7-1.46 (4H,m), 1.38 (6H,d). MS (ESI): M+H=619.

المصدر