Benzoyl chloride → N-Benzoyl-L-threonine methyl ester

HRID 2301006Notes

Reaction equation

HRID 2301006 reaction equation
Cl.[CH3:2][O:3][C:4](=[O:10])[C@H:5]([C@@H:7]([CH3:9])[OH:8])[NH2:6].C(N(CC)CC)C.[C:18](Cl)(=[O:25])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>CO>[CH3:2][O:3][C:4](=[O:10])[C@H:5]([C@@H:7]([CH3:9])[OH:8])[NH:6][C:18](=[O:25])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

5

Reactant 3

HCID 7412Benzoyl chlorideHCID 8471TriethylamineHCID 2734893Methyl L-threoninate hydrochloride

Product 1

HCID 736181N-Benzoyl-L-threonine methyl ester

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

3.00 g (17.7 mmol/1 eq) of L-threonine methyl ester hydrochloride are suspended in 50 ml of methanol, and 7.4 ml (53 mmol/3 eq) of triethylamine are added thereto. After 10 minutes, the mixture is cooled to 0° C. and the benzoyl chloride (2.74 g/190.5 mmol/1.1 eq) is added. Stirring is carried out at 0° C. for a further two hours. The solvent is then removed using a rotary evaporator. The solid that remains behind is taken up with ethyl acetate/H2O (50/20 ml). The aqueous phase is separated off and extracted by shaking twice more with ethyl acetate (30 ml each time). The combined organic phases are washed with 15 ml each of H2O and saturated sodium chloride solution, dried over magnesium sulfate and concentrated. 4.07 g (97% of theory) of a white solid are obtained.

Workup

  1. waitis carried out at 0° C. for a further two hours
  2. customThe solvent is then removed
  3. customa rotary evaporator
  4. customThe aqueous phase is separated off
  5. extractionextracted
  6. stirringby shaking twice more with ethyl acetate (30 ml each time)
  7. washThe combined organic phases are washed with 15 ml each of H2O and saturated sodium chloride solution
  8. dry with materialdried over magnesium sulfate
  9. concentrationconcentrated
  10. custom4.07 g (97% of theory) of a white solid are obtained

Sources & evidence

ORD record
ord-f3a6e50017bf46e4b758d12fcdf5d5d3
Source dataset
uspto-grants-2002_12
Patent number
US06498256B2

Reaction notes

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