Methyl chloroformate → (s)-2-((Methoxycarbonyl)amino)-2-phenylacetic acid

HRID 1471051

Reaction equation

HRID 1471051 reaction equation
[NH2:1][C@@H:2]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)[C:3]([OH:5])=[O:4].[OH-].[Na+].Cl[C:15]([O:17][CH3:18])=[O:16]>O1CCOCC1.CCOC(C)=O>[CH3:18][O:17][C:15]([NH:1][C@@H:2]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)[C:3]([OH:5])=[O:4])=[O:16]

Participants

6

Reactant 3

HCID 6586Methyl chloroformateHCID 14798Sodium HydroxideHCID 99291L-Phenylglycine

Product 1

HCID 14264559(s)-2-((Methoxycarbonyl)amino)-2-phenylacetic acidYield 51%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Procedure

To a solution of (S)-2-amino-2-phenylacetic acid (0.5 g, 3.31 mmol) in dioxane at 0° C. was added NaOH (5.46 g, 10.92 mmol) followed by dropwise addition of methyl chloroformate (0.51 mL, 6.62 mmol) and the solution was warmed to room temperature with stirring over 1 h. Diluted with EtOAc, washed with 1 N HCl, brine, dried (Na2SO4), filtered and removed solvent in vacuo to give the title compound (0.35 g, 1.673 mmol, 51%).

Workup

  1. washwashed with 1 N HCl, brine
  2. dry with materialdried (Na2SO4)
  3. filtrationfiltered
  4. customremoved solvent in vacuo

Sources & evidence

ORD record
ord-128ae61b2efe4ac882cad25c598a9e2c
Source dataset
uspto-grants-2015_04
Patent number
US09006387B2

Linked notes

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