Mannitol → Mannitol monocarbonate

Temperatur

0 °C

To a solution of astaxanthin 2E (0.100 g, 0.168 mmol) in DCM (4 mL) at 0° C. was added DIPEA (0.585 mL, 3.36 mmol), and 1,2,2,2-tetrachloroethyl chloroformate (0.103 mL, 0.672 mmol). The reaction mixture was stirred at 0° C. for 2 hours, then at room temperature for 1.5 hours, at which time (D)-mannitol (0.3060 g, 1.68 mmol), DMF (3 mL), and DMAP (0.2052 g, 1.68 mmol) were added to the reaction. The reaction mixture was stirred at room temperature for 24 hours, at which time the reaction was diluted with DCM, quenched with brine (20 mL), and then extracted with DCM. The combined organic layers were concentrated to yield mannitol monocarbonate (LVII) (10.19%) HPLC retention time: 9.474 min., 10.19% (AUC); LRMS (ESI) m/z (relative intensity): 827 (M++Na) (50), 804 (M+) (25), 725 (58), 613 (100), and astaxanthin 2E (53.73%).

1. waitat room temperature for 1.5 hours
2. stirringThe reaction mixture was stirred at room temperature for 24 hours, at which time the reaction
3. customquenched with brine (20 mL)
4. extractionextracted with DCM
5. concentrationThe combined organic layers were concentrated

ORD-Eintrag

ord-11cd7d05f7504de9892d27ca3e678ab7

Quelldatensatz

uspto-grants-2008_05

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US07375133B2