1,3-Dibromopropane → HCID 18439648, compound

A solution of (2S)-N-(4-hydroxy-5-methoxy-2-nitrobenzoyl)-4-fluoro pyrrolidine 2-carboxaldehyde diethylthioacetal VI (418 mg, 1 mmol), 1,3-dibromopropane (101 mg, 0.5 mmol) and K2CO3 (414 mg, 3 mmol) in dry acetone (40 ml) was refluxed for 48 h. After the completion of reaction as indicated by TLC, EtOAc-hexane (7:3), the reaction mixture was poured on to the water and then extracted with ethylacetate. Evaporation of the organic layer gave the crude product, which was further purified by column chromatography on silica gel eluting with EtOAc-hexane (1:1) to give the pure 1,1′-{[(Propane-1,3 diyl)dioxy]bis[2-nitro-5-methoxy-1,4-phenylene)carbonyl]}bis[4-fluoro pyrrolidine-2-carboxaldehyde diethylthioacetal] VII. H1 NMR (CDCl3, 200 MHz): δ 1.2–1.39 (m, 12H), 2.4–2.68 (m, 6H), 2.7–2.9 (m, 8H), 3.41–3.62 (m, 4H), 3.99 (s, 6H), 4.29–4.4 (m, 4H), 4.52 (d, j=3.9 Hz, 2H), 4.69–4.79 (m, 2H), 5.05 (t, 1H), 6.85 (s, 2H), 7.63 (s, 2H). FAB MASS: 877 (M+H)

1. customAfter the completion of reaction
2. extractionextracted with ethylacetate
3. customEvaporation of the organic layer
4. customgave the crude product, which
5. customwas further purified by column chromatography on silica gel eluting with EtOAc-hexane (1:1)

ORD record

ord-7fcef6278dc641bd9a1ee865e35b79c3

Source dataset

uspto-grants-2007_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07189710B2