Benzoyl chloride → HCID 683980, compound

HRID 1902176Notes

Reaction equation

HRID 1902176 reaction equation
Cl.[CH3:2][O:3][C:4](=[O:10])[C@H:5]([CH:7]([CH3:9])[CH3:8])[NH2:6].[C:11](Cl)(=[O:18])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.[OH-].[Na+]>O>[C:11]([NH:6][C@H:5]([C:4]([O:3][CH3:2])=[O:10])[CH:7]([CH3:9])[CH3:8])(=[O:18])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

5

Reactant 3

HCID 7412Benzoyl chlorideHCID 14798Sodium HydroxideHCID 111190Methyl valinate hydrochloride

Product 1

HCID 683980HCID 683980, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
25 °C

Procedure

To 4.0 g. L-valine methyl ester hydrochloride dissolved in 25 ml water was added 3.35 g. benzoyl chloride while keeping the pH of the solution at approximately 8-9 with 1 N NaOH. The addition of the reactants took approximately 2 hours. Following addition of the reactants the reaction mixture was stirred at about 25° C. for 4 hours and then cooled to about 0° C. for 16 hours. The precipitated solid was collected and the filtrate was extracted twice with ether. The above collected solid was dissolved in this ether solution, which was then washed with a saturated sodium bicarbonate solution. The organic phase was dried and concentrated to give a white solid.

Workup

  1. additionwas added 3.35 g
  2. additionThe addition of the reactants
  3. additionaddition of the reactants the reaction mixture
  4. temperaturecooled to about 0° C. for 16 hours
  5. customThe precipitated solid was collected
  6. extractionthe filtrate was extracted twice with ether
  7. customThe above collected solid
  8. dissolutionwas dissolved in this ether solution, which
  9. washwas then washed with a saturated sodium bicarbonate solution
  10. customThe organic phase was dried
  11. concentrationconcentrated
  12. customto give a white solid

Sources & evidence

ORD record
ord-bff0936a7b714e1f911f394719e0c290
Source dataset
uspto-grants-1982_12
Patent number
US04362550

Reaction notes

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