Water → 4-Iodo-6-[3,5-bis(trifluoromethyl)benzyl]-6,7,8,9-tetrahydro-5H-10-oxa-1,6-diazabenzocyclooctene-5-one

N-[3,5-bis(trifluoromethyl)benzyl]-2-chloro-N-(3-hydroxypropyl)-4-iodonicotinamide (6.86 g) was dissolved in tetrahydrofuran (60 mL). While the mixture was chilled on an ice bath, sodium hydride (581 mg, 60% oil suspension) was added and the mixture was stirred for 30 min. Subsequently, the temperature of the mixture was allowed to rise to room temperature and the mixture was stirred for another hour. While the mixture was chilled on an ice bath, water was added and the resulting mixture was extracted with ethyl acetate. The extract was washed with a saturated aqueous solution of sodium chloride and was then dried on anhydrous sodium sulfate. The solvent was removed and the resulting residue was purified on a silica gel column chromatography (ethyl acetate:n-hexane=2:1) to obtain 5-[3,5-bis(trifluoromethyl)benzyl]-7-iodo-6-oxo-2,3,4,5-tetrahydro-6H-pyrido[2,3-b][1,5]oxazocine (2.69 g, 42%).

1. temperatureWhile the mixture was chilled on an ice bath
2. customto rise to room temperature
3. stirringthe mixture was stirred for another hour
4. temperatureWhile the mixture was chilled on an ice bath
5. extractionthe resulting mixture was extracted with ethyl acetate
6. washThe extract was washed with a saturated aqueous solution of sodium chloride
7. dry with materialwas then dried on anhydrous sodium sulfate
8. customThe solvent was removed
9. customthe resulting residue was purified on a silica gel column chromatography (ethyl acetate:n-hexane=2:1)

ORD-Eintrag

ord-9004ec94212943e0a72bf4bd85d5283d

Quelldatensatz

uspto-grants-2006_04

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US07030107B2