Methanol → Methyl phenylglycinate, L-

HRID 525353

Reaction equation

HRID 525353 reaction equation
S(=O)(=O)(O)O.[NH2:6][C@@H:7]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[C:8]([OH:10])=[O:9].[CH3:17]O>>[NH2:6][C@@H:7]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[C:8]([O:10][CH3:17])=[O:9]

Participants

4

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 99291L-Phenylglycine

Product 1

HCID 1201451Methyl phenylglycinate, L-Yield 74%

Conditions

Temperature
65 °C

Procedure

A catalytic amount of concentrated sulfuric acid (0.1 mL) was added to a 50 mL round bottom flask containing a solution of (S)-2-amino-2-phenylacetic acid (commercially available from Sigma-Aldrich, Milwaukee, Wis.) (1.0 g, 6.6 mmol) in MeOH (10 mL). The resulting mixture was heated at 65° C. for 6 hours. The solvent was removed under reduced pressure, and the mixture was quenched with aqueous NaHCO3 and extracted with EtOAc. The organic layer was dried over Na2SO4, filtered, and concentrated to afford (S)-methyl 2-amino-2-phenylacetate (0.8 g, 74.0%) as a white solid. 1H NMR (300 MHz, CDCl3) δ: 7.37-7.32 (m, 5H), 4.62 (s, 1H), 3.70 (s, 3H).

Workup

  1. customThe solvent was removed under reduced pressure
  2. customthe mixture was quenched with aqueous NaHCO3
  3. extractionextracted with EtOAc
  4. dry with materialThe organic layer was dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-e1bad738b63341ebac6fef4a45569663
Source dataset
uspto-grants-2016_05
Patent number
US09340549B2

Linked notes

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