Sodium Hydroxide → 2-(N-methyl-3-phenylprop-2-ynoylamino)acetic acid

HRID 1837964Notes

Reaction equation

HRID 1837964 reaction equation
[CH3:1][N:2]([C:9](=[O:18])[C:10]#[C:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[CH2:3][C:4]([O:6]CC)=[O:5].[OH-].[Na+]>CO.O>[CH3:1][N:2]([C:9](=[O:18])[C:10]#[C:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[CH2:3][C:4]([OH:6])=[O:5]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 11390917ethyl 2-(N-methyl-3-phenylprop-2-ynoylamino)acetate

Product 1

HCID 226776402-(N-methyl-3-phenylprop-2-ynoylamino)acetic acidYield 93%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a 0° C. solution of ethyl 2-(N-methyl-3-phenylprop-2-ynoylamino)acetate (prepared according to the procedure described for Intermediate A, 124.4 g, 0.507 mol) in MeOH (750 mL) was added a solution of NaOH (30.4 g, 0.760 mol, 1.5 equiv) in water (1000 mL). The resulting red reaction mixture was stirred for 20 min, then allowed to warm to room temperature and stirred for 2 h. The reaction was washed with CH2Cl2 (3×500 mL). The aqueous layer was cooled in an ice bath and acidified to pH 3 using conc. HCl. A light orange oil formed, which was extracted into EtOAc (4×500 mL). The combined EtOAc layers were washed with water (3×200 mL) and a saturated NaCl solution (2×300 mL), dried (Na2SO4) and concentrated under reduced pressure to give 2-(N-methyl-3-phenylprop-2-ynoylamino)acetic acid (102.5 g, 93%) as an orange solid: TLC (1% AcOH/5% MeOH/CH2Cl2) Rf 0.20; 1H NMR (CDCl3) δ 3.09 (s, 1.1H, N—CH3), 3.36 (s, 1.9H, N—CH3), 4.27 (s, 1.2H, N—CH3), 4.45 (s, 0.8H, N—CH3), 7.30-7.56 (m, 5H), 9.58 (br s, 1H).

Workup

  1. stirringstirred for 2 h
  2. washThe reaction was washed with CH2Cl2 (3×500 mL)
  3. temperatureThe aqueous layer was cooled in an ice bath
  4. customA light orange oil formed
  5. extractionwhich was extracted into EtOAc (4×500 mL)
  6. washThe combined EtOAc layers were washed with water (3×200 mL)
  7. dry with materiala saturated NaCl solution (2×300 mL), dried (Na2SO4)
  8. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-5d17491d42d64f2896e28d6c83073cfa
Source dataset
uspto-grants-2004_08
Patent number
US06784167B2

Reaction notes

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