Hydrochloric Acid → (R)-2-Acetylamino-3-methoxy-propionic acid

HRID 2280359Notes

Reaction equation

HRID 2280359 reaction equation
[C:1]([NH:4][CH:5]([C:9]([OH:11])=[O:10])[CH2:6][O:7][CH3:8])(=[O:3])[CH3:2].[OH-].[Na+].Cl>O>[C:1]([NH:4][C@H:5]([CH2:6][O:7][CH3:8])[C:9]([OH:11])=[O:10])(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 189180482-Acetamido-3-methoxypropanoic acid

Product 1

HCID 10558933(R)-2-Acetylamino-3-methoxy-propionic acidYield 50%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
25 °C

Procedure

In a vessel, equipped with a magnetic stirrer and pH controller, N-acetyl-O-methyl-D,L-serine (3 g) was dissolved in demineralized water (30 mL) and the pH was adjusted to 7.5-8.0 with 5N sodium hydroxide solution. Acylase I from Porcine Kidney (EC: 3.5.1.14) (50 mg) was added and the solution maintained at 25° C. under mild agitation overnight. The pH was adjusted to 2.7 with concentrated HCl and the aqueous solution injected onto Dowex™ 50WX4-50 ion exchange resin (50 mL) conditioned at pH 3.8. The resulting material was eluted with water at pH 2.4. The aqueous solution thereby obtained was then evaporated to dryness under vacuum to afford the title compound (1.5 g, 50%) as an off-white solid.

Workup

  1. customIn a vessel, equipped with a magnetic stirrer
  2. additionAcylase I from Porcine Kidney (EC: 3.5.1.14) (50 mg) was added
  3. washThe resulting material was eluted with water at pH 2.4
  4. customThe aqueous solution thereby obtained
  5. customwas then evaporated to dryness under vacuum

Sources & evidence

ORD record
ord-d3a07d20d77c47be9b81a14f76a28436
Source dataset
uspto-grants-2015_09
Patent number
US09139513B2

Reaction notes

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