Acetic Anhydride → 2-Acetamido-3-methoxypropanoic acid

HRID 2280358Notes

Reaction equation

HRID 2280358 reaction equation
[CH3:1][O:2][CH2:3][CH:4]([C:6]([OH:8])=[O:7])[NH2:5].[O:9]1CC[CH2:11][CH2:10]1.C(OC(=O)C)(=O)C>O>[C:10]([NH:5][CH:4]([C:6]([OH:8])=[O:7])[CH2:3][O:2][CH3:1])(=[O:9])[CH3:11]

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 8028TetrahydrofuranHCID 97963DL-O-Methylserine

Product 1

HCID 189180482-Acetamido-3-methoxypropanoic acidYield 90%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Into a vessel, equipped with a mechanical stirrer, was added O-methyl-D,L-serine (1.0 eq.) at 20° C. Tetrahydrofuran (6 volumes) and water (0.65 volume) were added. Acetic anhydride (1.2 eq.) was added dropwise over 5 minutes. The white suspension was stirred mechanically until complete conversion was observed by HPLC monitoring (approximately 16 h), by which time the reaction mixture had become homogeneous. The tetrahydrofuran and water were removed azeotropically. Toluene was added in order to effect complete removal of water and acetic acid (KF and GC control). The wet solid was dried at 40° C. under vacuum overnight. The title compound (90% yield) was obtained as a white solid with a chemical purity of >98% as measured by HPLC.

Workup

  1. customInto a vessel, equipped with a mechanical stirrer
  2. customwas observed by HPLC monitoring (approximately 16 h), by which time
  3. customThe tetrahydrofuran and water were removed azeotropically
  4. additionToluene was added in order
  5. customremoval of water and acetic acid (KF and GC control)
  6. customThe wet solid was dried at 40° C. under vacuum overnight

Sources & evidence

ORD record
ord-ce3deb91c6e44d679e0608cff648fd9e
Source dataset
uspto-grants-2015_09
Patent number
US09139513B2

Reaction notes

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