Acetic Acid → HCID 178502507, Verbindung

(S)-2-Methoxycarbonylamino-3-methylbutyric acid (9.6 mg, 54.5 μmol) and HATU (23.5 mg, 62 μmol) were stirred in DCM (1.0 mL, 16 mmol) for 10 minutes. (R)-3-[N-(3′-Chlorobiphenyl-4-ylmethyl)-N′-(3-hydroxyisoxazole-5-carbonyl)hydrazino]-2-hydroxypropionic acid 2-oxo-2-phenylethyl ester (20.0 mg, 36.4 μmol) and DIPEA (31.7 μL, 182 μmol) were added, and the resulting mixture was stirred at room temperature overnight. The mixture was then concentrated and purified by flash chromatography (EtOAc/hexanes=0-100%). Zinc (119 mg, 1.8 mmol) and AcOH (0.5 mL, 9 mmol) were added. The mixture was stirred for 2 hours and filtered. The solids were washed with AcOH (1 mL) and filtered. The combined filtrates were purified by reverse phase preparative HPLC to yield the title compound (0.8 mg). MS m/z [M+H]+ calc'd for C27H29ClN4O9, 589.16. found 589.3.

1. concentrationThe mixture was then concentrated
2. custompurified by flash chromatography (EtOAc/hexanes=0-100%)
3. stirringThe mixture was stirred for 2 hours
4. filtrationfiltered
5. washThe solids were washed with AcOH (1 mL)
6. filtrationfiltered
7. customThe combined filtrates were purified by reverse phase preparative HPLC

ORD-Eintrag

ord-2b788c461d3c4007b4b1a6a6c68f88fb

Quelldatensatz

uspto-grants-2014_10

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08871792B2