Water → N-Benzoyl-L-threonine methyl ester

HRID 1840653Notes

Reaction equation

HRID 1840653 reaction equation
[C:1](Cl)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.[CH3:11][O:12][C:13](=[O:19])[C@H:14]([C@@H:16]([CH3:18])[OH:17])[NH2:15].O.C(=O)(O)[O-].[Na+]>C(OCC)(=O)C>[CH3:11][O:12][C:13](=[O:19])[C@H:14]([C@@H:16]([CH3:18])[OH:17])[NH:15][C:1](=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7412Benzoyl chlorideHCID 516892Sodium BicarbonateHCID 2734893Methyl L-threoninate hydrochloride

Product 1

HCID 736181N-Benzoyl-L-threonine methyl esterYield 93.2%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

A solution of benzoyl chloride (17 g) in ethyl acetate (40 ml) is added dropwise, with stirring, in an ice-cold mixture of L-threonine methyl ester, hydrochloride (16.5 g), water (100 ml), sodium bicarbonate (21.8 g), and ethyl acetate (100 ml). After stirring for 2 hours, the organic phase is separated, dried over sodium sulfate, and evaporated to give crystalline N-benzoyl-L-threonine methyl ester (21.5 g).

Workup

  1. customthe organic phase is separated
  2. dry with materialdried over sodium sulfate
  3. customevaporated

Sources & evidence

ORD record
ord-a143e3c3a8cd428a8703c6644ee5eee9
Source dataset
uspto-grants-2004_01
Patent number
US06680387B2

Reaction notes

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