Methanol → (4R)-4-Hydroxy-L-proline methyl ester

반응식

S(Cl)(Cl)=O.[OH:5][C@H:6]1[CH2:10][NH:9][C@H:8]([C:11]([OH:13])=[O:12])[CH2:7]1.[CH3:14]O>>[OH:5][C@H:6]1[CH2:10][NH:9][C@H:8]([C:11]([O:13][CH3:14])=[O:12])[CH2:7]1

참가 물질

반응물 3

HCID 887Methanol

HCID 5810L-Hydroxyproline

HCID 24386Thionyl Chloride

생성물 1

HCID 7015125(4R)-4-Hydroxy-L-proline methyl ester

반응 조건

온도: 0 °C

실험 절차

Thionyl chloride (270 mL) was added dropwise to methanol (1500 mL) over 1 hour, followed by the addition of (4R)-4-hydroxy-L-proline (150 g). The mixture was stirred at reflux for 36 hours, and then concentrated under reduced pressure. Methanol (1500 mL) was added, followed by a slow addition of triethylamine (310 mL). The mixture was cooled to 0° C., filtered, and the filtrate was concentrated to afford methyl (4R)-4-hydroxy-L-prolinate. The residue was used directly without further purification.