Methanol → (2R)-3-benzyloxy-2-aminopropanoic acid methyl ester

Temperatur

0 °C

To a solution of BOC-O-benzyl-D-serine (5.05 g, 17.12 mmol) in MeOH (100 mL) at −78° C., was added SOCl2 dropwise. The reaction mixture was warmed to 0° C. and stirred for ˜4 hours and then concentrated. The residue was taken up in EtOAc and washed with 10% Na2CO3 (3×80 mL). The organic layer was dried over sodium sulfate, filtered and concentrated. To the crude material in EtOAc (100 mL) at 0° C. was bubbled HCl gas for approximately 10 minutes, and the reaction was capped and the mixture stirred at 0° C. for 30 minutes before it was concentrated in vacuo. The crude material was diluted with 50 mL of a 1:1 solution of saturated NaHCO3/10% Na2CO3 and extracted with EtOAc (4×50 mL). The combined organics were dried over sodium sulfate, filtered, and concentrated to give O-benzyl-D-serine methyl ester (3.13 g, 14.96 mmol) which was used without further purification. LCMS (ES) m/z 210.1 (M+H)+.

1. concentrationconcentrated
2. washwashed with 10% Na2CO3 (3×80 mL)
3. dry with materialThe organic layer was dried over sodium sulfate
4. filtrationfiltered
5. concentrationconcentrated
6. customTo the crude material in EtOAc (100 mL) at 0° C. was bubbled HCl gas for approximately 10 minutes
7. customthe reaction was capped
8. stirringthe mixture stirred at 0° C. for 30 minutes before it
9. concentrationwas concentrated in vacuo
10. additionThe crude material was diluted with 50 mL of a 1:1 solution of saturated NaHCO3/10% Na2CO3
11. extractionextracted with EtOAc (4×50 mL)
12. dry with materialThe combined organics were dried over sodium sulfate
13. filtrationfiltered
14. concentrationconcentrated

ORD-Eintrag

ord-2bb93f053a704df6beb1299f45b00afe

Quelldatensatz

uspto-grants-2005_06

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US06908921B2