Hydrochloric Acid → Methyl 3-amino-2-hydroxypropanoate hydrochloride

HRID 456356

Reaction equation

HRID 456356 reaction equation
[NH2:1][CH2:2][CH:3]([C:5]([OH:7])=[O:6])[OH:4].[ClH:8].[CH3:9]O>>[ClH:8].[NH2:1][CH2:2][CH:3]([OH:4])[C:5]([O:7][CH3:9])=[O:6]

Participants

4

Reactant 3

HCID 313Hydrochloric Acid2×HCID 887MethanolHCID 11267Isoserine

Product 1

HCID 71757671Methyl 3-amino-2-hydroxypropanoate hydrochlorideYield 92%

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.

Workup

  1. dissolutionThe solid material slowly dissolved
  2. customto yield a pale yellow liquid after a few minutes
  3. customExcess HCl gas was removed
  4. customby bubbling nitrogen into the reaction mixture
  5. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-5900908fc15b4ae7bf9e222a9ccf2e3c
Source dataset
uspto-grants-2007_03
Patent number
US07186397B2

Linked notes

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