Benzene → 4-Chloro-2-(3-chloropropylamino)-6-methyl-10,10dioxo-10,11-dihydro-5-oxa-10lambda*6*-thia-dibenzo[a,d]-cycloheptene-8-carboxylic acid methyl ester

Powdered sodium-borohydride (0.93 g, 24 mmol) was added in portions at 0° C., to a solution of chloropropionic acid (5.32 g, 49 mmol) in THF (13 mL), and benzene (210 mL). Reaction mixture was warmed to room temperature and stirred for 1 h, and compound of Example 1 (3.0 g, 8.17 mmol) was added. Reaction mixture was refluxed for 3 h. Reaction mixture was cooled and quenched using sodium bicarbonate solution, and extracted with ethylacetate. Organic layer was washed with water (100 mL) and brine (50 mL). The crude product obtained was purified by column chromatography (silica gel, ethylacetate/pet. ether) to obtain the title compound. Yield: 3.7 g (99%); 1H NMR (DMSO-d6, 300 MHz): δ 1.96 (q, 2H, CH2), 2.62 (s, 3H, CH3), 3.11 (q, 2H, CH2), 3.72 (t, 2H, CH2), 3.85 (s, 3H, OCH3), 5.12 (s, 2H, CH2), 6.29 (s, 1H, Ar), 6.31 (s, 1H, Ar), 8.07 (s, 1H, Ar), 8.13 (s, 1H, Ar); MS: m/e (El) 443 (M+).

1. customReaction mixture
2. customReaction mixture
3. temperaturewas refluxed for 3 h
4. customReaction mixture
5. temperaturewas cooled
6. customquenched
7. extractionextracted with ethylacetate
8. washOrganic layer was washed with water (100 mL) and brine (50 mL)
9. customThe crude product obtained
10. customwas purified by column chromatography (silica gel, ethylacetate/pet. ether)

ORDレコード

ord-ea83bf9e38b2404899550e3789ed9fb3

出典データセット

uspto-grants-2012_04

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US08163730B2