Sodium Bicarbonate → (S)-Methyl 3-([1,1'-biphenyl]-4-yl)-2-aminopropanoate

HRID 1655283Notes

Reaction equation

HRID 1655283 reaction equation
Cl.[CH3:2][O:3][C:4](=[O:20])[C@@H:5]([NH2:19])[CH2:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[CH:9][CH:8]=1.C(=O)(O)[O-].[Na+]>O>[CH3:2][O:3][C:4](=[O:20])[C@@H:5]([NH2:19])[CH2:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[CH:9][CH:8]=1

Participants

4

Reactant 2

HCID 516892Sodium BicarbonateHCID 45357110methyl (2S)-2-amino-3-(4-phenylphenyl)propanoate hydrochloride

Product 1

HCID 15714801(S)-Methyl 3-([1,1'-biphenyl]-4-yl)-2-aminopropanoate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a suspension of (S)-2-amino-3-(biphenyl-4-yl)-propionic acid methyl ester hydrochloride (J. Org. Chem., 1992, 57, 379; 10 g, 34.3 mmol) in water (200 mL) is added solid sodium bicarbonate (3.17 g, 37.7 mmol). The mixture is stirred for 30 minutes and then extracted with ether (3×80 mL). The combined organic phases are washed with brine (50 mL) and then dried over anhydrous magnesium sulfate. Evaporation of the solvent in vacuo affords (S)-2-amino-3-(biphenyl-4-yl)-propionic acid methyl ester as a white solid.

Workup

  1. extractionextracted with ether (3×80 mL)
  2. washThe combined organic phases are washed with brine (50 mL)
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customEvaporation of the solvent in vacuo

Sources & evidence

ORD record
ord-010a7c2a55c6435a9e9a8101528b1154
Source dataset
uspto-grants-1993_10
Patent number
US05250522

Reaction notes

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