Reacción #543538

ord-5900908fc15b4ae7bf9e222a9ccf2e3c

Ecuación de reacción

NCC(O)C(=O)O
isoserine
CO
methanol
Cl
HCl
Cl
HCl
COC(=O)C(O)CN.Cl
product
Rendimiento 92.0%
COC(=O)C(O)CN.Cl
Methyl 3-amino-2-hydroxypropionate hydrochloride
Rendimiento 92.0%

Reactivos

Ninguno

Condiciones de reacción

Condiciones detalladas
See reaction.notes.procedure_details.

Tratamiento posterior

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

Procedimiento

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.

Fuente

DOI: 10.6084/m9.figshare.5104873.v1Patente: US07186397B2uspto-grants-2007_03