Benzoyl chloride → Nalpha-benzoyl-O-benzyl-threonine

HRID 2308768Notes

Reaction equation

HRID 2308768 reaction equation
[CH2:1]([O:8][C@H:9]([CH3:15])[C@@H:10]([C:12]([OH:14])=[O:13])[NH2:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([O-])([O-])=O.[Na+].[Na+].[C:22](Cl)(=[O:29])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>O.O1CCCC1>[C:22]([NH:11][C@H:10]([C:12]([OH:14])=[O:13])[C@@H:9]([CH3:15])[O:8][CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)(=[O:29])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Participants

6

Reactant 3

HCID 7412Benzoyl chlorideHCID 10340Sodium CarbonateHCID 6951054O-BENZYL-L-THREONINE

Product 1

HCID 54081094Nalpha-benzoyl-O-benzyl-threonine

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

A mixture containing 10 mmoles of O-benzyl-threonine, 10 mmoles of Na2CO3 in water and tetrahydrofuran (THF) is stirred at room temperature. Benzoyl chloride (10 mmoles), dissolved in anhydrous THF, is added gradually with continued stirring at room temperature. The reaction mixture is stirred until the reaction is completed as judged by thin layer chromatography (TLC). The solvent is removed by a rotary evaporator at 30° C. An excess of water is added and the reaction mixture extracted several times with ethyl acetate. The aqueous phase is adjusted to pH 2 with 1N HCl. The precipitate is recovered by filtration and washed with dilute HCl and then with cold water. The precipitate is dried over P2O5 in a vacuum desiccator. The precipitate is homogeneous as judged by TLC. In this reaction sequence, the racemate is obtained.

Workup

  1. additionis added gradually
  2. stirringwith continued stirring at room temperature
  3. stirringThe reaction mixture is stirred until the reaction
  4. customThe solvent is removed by a rotary evaporator at 30° C
  5. additionAn excess of water is added
  6. extractionthe reaction mixture extracted several times with ethyl acetate
  7. filtrationThe precipitate is recovered by filtration
  8. washwashed with dilute HCl
  9. dry with materialThe precipitate is dried over P2O5 in a vacuum desiccator
  10. customIn this reaction sequence, the racemate is obtained

Sources & evidence

ORD record
ord-93d63a18dc1f4251b3a7830711dc473e
Source dataset
uspto-grants-1987_09
Patent number
US04690936

Reaction notes

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