Water → D-Threonine, N-benzoyl-, methyl ester

HRID 2384571Notes

Reaction equation

HRID 2384571 reaction equation
[CH3:1][O:2][C:3](=[O:9])[C@@H:4]([C@H:6]([CH3:8])[OH:7])[NH2:5].[C:10](Cl)(=[O:17])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.O>CO>[CH3:1][O:2][C:3](=[O:9])[C@@H:4]([C@H:6]([CH3:8])[OH:7])[NH:5][C:10](=[O:17])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

5

Reactant 3

HCID 962WaterHCID 7412Benzoyl chlorideHCID 100312HCID 100312, compound

Product 1

HCID 736182D-Threonine, N-benzoyl-, methyl esterYield 104.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
12 °C

Procedure

A crude D-threonine methyl ester (39.49 g) was dissolved in 300 mL of methanol and than transferred to the 1 L 3-neck round bottom flask equipped with a thermocouple, magnetic stirrer and cooling ice bath. A solution was chilled to 12° C., and a total of 64.1 g (0.63 mol, 3 eq.) was added to the flask and then cooled to −10° C. A total of 30.9 g (0.21 mol) of benzoyl chloride was added to the solution and resulting mixture stirred at 0° C. for 1 hour. After this period of time the solvent was removed on rotovap to yield a viscous semi-solid. A total of 300 mL of cold water was added to the residue and organic material was extracted with ethyl acetate (2×300 mL). The organic phase was separated, washed with brine (200 mL) and dried over sodium sulfate. The solvent was removed on rotovap to yield 52.02 g (104%) of a clear yellow oil with Rf=0.39 in EtOAc/hexane=6:4). Obtained oil was crystallized from 200 mL of ether to give a white solid, which was filtered off, washed with hexane (2×100 mL) and dried under suction. An additional drying in a vacuum desiccator yielded 42.35 g (84.7% yield in 2 steps).

Workup

  1. customequipped with a thermocouple, magnetic stirrer
  2. temperaturecooling ice bath
  3. additiona total of 64.1 g (0.63 mol, 3 eq.) was added to the flask
  4. temperaturecooled to −10° C
  5. customresulting mixture
  6. customAfter this period of time the solvent was removed on rotovap
  7. customto yield a viscous semi-solid
  8. extractionwas extracted with ethyl acetate (2×300 mL)
  9. customThe organic phase was separated
  10. washwashed with brine (200 mL)
  11. dry with materialdried over sodium sulfate
  12. customThe solvent was removed on rotovap

Sources & evidence

ORD record
ord-96fe8d5f9f884e99bd072efd5cf3a52d
Source dataset
uspto-grants-2012_09
Patent number
US08263790B2

Reaction notes

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