DL-O-Methylserine → O-Methyl-D-serine

HRID 2280356Notes

Reaction equation

HRID 2280356 reaction equation
[CH3:1][O:2][CH2:3][CH:4]([C:6]([OH:8])=[O:7])[NH2:5].[C:9]([N:12]([C:18]1[C:27]2[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=2)[CH:21]=[CH:20][CH:19]=1)[C@@H:13]([C:15]([OH:17])=[O:16])[CH3:14])(=[O:11])[CH3:10]>C(O)C>[C:9]([N:12]([C:18]1[C:27]2[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=2)[CH:21]=[CH:20][CH:19]=1)[C@@H:13]([C:15]([OH:17])=[O:16])[CH3:14])(=[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 69671538N-acetyl-(R)-naphthylalanine

Product 2

HCID 88251O-Methyl-D-serineYield 128%HCID 69671538N-acetyl-(R)-naphthylalanine

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

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 ethanol (150 mL). N-Acetyl-(R)-naphthylalanine (10.80 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 ethanol (5 mL) and dried at 40° C. under vacuum for 3 h. Crude N-acetyl-(R)-naphthylalanine salt of O-methyl-D-serine (6.4 g, 40.5%) was obtained as a white solid with a chiral purity >90%. A portion (5 g) of this solid was suspended in ethanol (30 mL), heated to 50° C. for 4 h, cooled to room temperature and filtered. The resulting solid was rinsed with ethanol (5 mL) and dried at 40° C. under vacuum for 3 h. Pure N-acetyl-(R)-naphthylalanine salt of O-methyl-D-serine (4.6 g, 91.5%) was obtained as a white solid with a chiral purity >95%. 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 ethanol (5 mL)
  6. customdried at 40° C. under vacuum for 3 h

Sources & evidence

ORD record
ord-de7f1b86f1aa4e79a1e58647e1118d51
Source dataset
uspto-grants-2015_09
Patent number
US09139513B2

Reaction notes

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