Methanol → D-Serine methyl ester hydrochloride
Reaction equation
[NH2:1][C@H:2]([CH2:6][OH:7])[C:3]([OH:5])=[O:4].S(Cl)([Cl:10])=O.[CH3:12]O>>[ClH:10].[NH2:1][C@H:2]([CH2:6][OH:7])[C:3]([O:5][CH3:12])=[O:4]Participants
4
Procedure
To a solution of (R)-2-amino-3-hydroxypropanoic acid (105 g, 1 mol) in methanol (1200 mL) was added thionyl chloride (87.6 mL, 142.8 g, 1.2 mol) dropwise at 0° C. After addition, the reaction mixture was heated at reflux for 12 h. Volatiles were evaporated to give the (R)-methyl 2-amino-3-hydroxypropanoate hydrochloride salt (155 g, yield 100%) as a solid that was used in the next step without further purification. 1H NMR (CDCl3, 400 MHz) δ 8.51 (brs, 2H), 4.08 (s, 1H), 3.79 (m, 2H), 3.71 (s, 3H).
Workup
- additionAfter addition
- temperaturethe reaction mixture was heated
- temperatureat reflux for 12 h
- customVolatiles were evaporated
Sources & evidence
- ORD record
- ord-ab1f6cd0e2fc4c4f96dba2b98ac0e642
- Source dataset
- uspto-grants-2013_07
- Patent number
- US08487108B2
Reaction notes
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