DL-O-Methylserine → O-Methyl-D-serine

HRID 2280355Notes

Reaction equation

HRID 2280355 reaction equation
[CH3:1][O:2][CH2:3][CH:4]([C:6]([OH:8])=[O:7])[NH2:5].[C:9]([NH:12][C@@H:13]([C:21]([OH:23])=[O:22])[CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)(=[O:11])[CH3:10]>CO.O>[C:9]([NH:12][C@@H:13]([C:21]([OH:23])=[O:22])[CH2:14][C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1)(=[O:11])[CH3:10].[CH3:1][O:2][CH2:3][C@H:4]([C:6]([OH:8])=[O:7])[NH2:5]

Participants

5

Reactant 2

HCID 97963DL-O-MethylserineHCID 101184(-)-N-Acetylphenylalanine

Product 2

HCID 88251O-Methyl-D-serineYield 68%HCID 101184(-)-N-Acetylphenylalanine

Reagents, catalysts & solvents 1

HCID 22242641Methanol--water (1/1)Solvent

Conditions

Temperature
50 °C

Procedure

Into a 250 mL round-bottomed flask equipped with a stirrer, reflux condenser and thermometer was added O-methyl-D,L-serine (5 g) in 90:10 methanol/water (25 mL). N-Acetyl-D-phenylalanine (8.70 g) was added in one portion and the mixture heated to 50° C. overnight. The suspension was cooled to room temperature and filtered, and the solid was rinsed with 90:10 methanol/water (5 mL) and dried at 40° C. under vacuum for 3 h. The N-acetyl-D-phenylalanine salt of O-methyl-D-serine (3.4 g, 25%) was obtained as a white solid with a chiral purity >90%. Regeneration of the title compound could be effected by adjustment of the pH to 1-2 by treatment with HCl, followed by extraction into an organic solvent and subsequent adjustment of the pH to ˜7 with NaOH.

Workup

  1. customInto a 250 mL round-bottomed flask equipped with a stirrer
  2. temperaturereflux condenser
  3. temperatureThe suspension was cooled to room temperature
  4. filtrationfiltered
  5. washthe solid was rinsed with 90:10 methanol/water (5 mL)
  6. customdried at 40° C. under vacuum for 3 h

Sources & evidence

ORD record
ord-7cc8fffb54f24a93afe5b60a277cf741
Source dataset
uspto-grants-2015_09
Patent number
US09139513B2

Reaction notes

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