1,2-Dichloroethane → HCID 68674801, Verbindung

1-hydroxybenzotriazole (225 mg, 1.65 mmol) and EDC (315 mg, 1.65 mmol) were added sequentially to compound 50.3 (750 mg, 1.5 mmol) in dichloromethane (25 mL). The resulting mixture was stirred for 1 h before ammonium hydroxide (25% in water, 630 mg, 4.5 mmol) was added dropwise. The reaction was quenched after 30 min. with water (10 mL). The reaction mixture was extracted with dichloromethane (10 mL×3). The organic extracts were combined, dried over MgSO4 and concentrated under reduced pressure. The product was purified via flash chromatography (50% ethyl acetate in hexanes) to yield 51.1 (720 mg) as a white solid. MS ESI (pos.) m/e: 500 (M+H). 1H NMR (400 MHz) (CDCl3) δ 7.72 (4H, s); 7.68 (1H, s); 7.57-7.48 (3H, m); 7.29-7.25 (2H, m); 7.0-6.97 (2H, d, J=6.8 Hz); 5.14 (2H, s); 3.91-3.88 (1H, m); 3.19-3.13 (1H, m); 2.60-2.55 (1H, m); 1.4 (9H, s).

1. additionwas added dropwise
2. customThe reaction was quenched after 30 min. with water (10 mL)
3. extractionThe reaction mixture was extracted with dichloromethane (10 mL×3)
4. dry with materialdried over MgSO4
5. concentrationconcentrated under reduced pressure
6. customThe product was purified via flash chromatography (50% ethyl acetate in hexanes)

ORD-Eintrag

ord-d602dfaebdae47c48f95644970eb1321

Quelldatensatz

uspto-grants-2010_01

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US07649110B2