Diisopropylethylamine → HCID 59486385, Verbindung

To an ice-cold solution of acid S3 (0.612 mmol) and DIPEA (1.3 mmol) in THF (2.5 ml) was added HATU (0.612 mmol) and the reaction mixture was stirred for 15 min. Then a solution of amine A12 (0.735 mmol) in THF (1 ml) was added slowly and allowed to stir at 25° C. for 16 h. The reaction mixture was concentrated under reduced pressure and diluted with water (50 ml) and extracted with ethyl acetate (2×50 ml). The organic layer was washed with water, brine, dried over anhydrous Na2SO4 and concentrated. The crude product was purified by column chromatography using 1-5% MeOH in DCM as eluent. Yield: 50% 2. To a solution of step-1 product (180 mg) in MeOH (5 ml) was added 1N NaOH solution (5 ml) at 0° C. Then the reaction mixture was stirred at 25° C. for 16 h. The reaction mixture was diluted with water and extracted with ethyl acetate. The organic layer was washed with water, brine, dried over anhydrous Na2SO4 and concentrated. The crude product was purified by column chromatography on neutral alumina using 1-10% MeOH in DCM as eluent. m/z=530.7 [MH]+

1. stirringto stir at 25° C. for 16 h
2. concentrationThe reaction mixture was concentrated under reduced pressure
3. additiondiluted with water (50 ml)
4. extractionextracted with ethyl acetate (2×50 ml)
5. washThe organic layer was washed with water, brine
6. dry with materialdried over anhydrous Na2SO4
7. concentrationconcentrated
8. customThe crude product was purified by column chromatography

ORD-Eintrag

ord-198a620cb28d413ca028cb195e9d6696

Quelldatensatz

uspto-grants-2012_04

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08158628B2