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

(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).

1. concentrationThe reaction mixture was concentrated under vacuum to a residue
2. additiondiluted with ethyl acetate (2 mL)
3. washThe reaction was washed in distilled water
4. dry with materialbrine, and was dried over magnesium sulfate
5. concentrationThe dried solution was then concentrated to an oil
6. custompurified by silica gel chromatography (2:1 hexanes/ethyl acetate)

ORD record

ord-5459526d93d048d584966c8d36ce887a

Source dataset

uspto-grants-2008_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07419967B2