Reaction #543538

Reaction equation

isoserine

methanol

HCl

HCl

→

product

Yield 92.0%

Methyl 3-amino-2-hydroxypropionate hydrochloride

Yield 92.0%

Conditions

Workup

1. 1
   workup.DISSOLUTIONThe solid material slowly dissolved
2. 2
   Otherto yield a pale yellow liquid after a few minutes
3. 3
   OtherExcess HCl gas was removed
4. 4
   Otherby bubbling nitrogen into the reaction mixture
5. 5
   Otherthe solvent was removed under reduced pressure

Procedure

A suspension of isoserine (18) (20.0 g, 0.19 mol) in anhydrous methanol (100 mL) was saturated with HCl gas at 0° C. while being stirred with exclusion of moisture. The solid material slowly dissolved to yield a pale yellow liquid after a few minutes. The HCl saturated solution was stirred overnight (20 h) at room temperature. Excess HCl gas was removed by bubbling nitrogen into the reaction mixture and the solvent was removed under reduced pressure to yield the product as a syrup (27.1 g; yield 92%) Mass Spectrum M+H 120. The product was immediately taken to the next step without further purification.

Source