Hydrochloric Acid → (S)-2-CHLORO-4-METHYL-N-VALERIC ACID

HRID 1088194Notes

Reaction equation

HRID 1088194 reaction equation
N[C@H:2]([C:7]([OH:9])=[O:8])[CH2:3][CH:4]([CH3:6])[CH3:5].[ClH:10].NC(N)=O>[N+]([O-])(O)=O>[Cl:10][C@@H:2]([CH2:3][CH:4]([CH3:6])[CH3:5])[C:7]([OH:9])=[O:8]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 1176UreaHCID 6106L-Leucine

Product 1

HCID 12732683(S)-2-CHLORO-4-METHYL-N-VALERIC ACID

Reagents, catalysts & solvents 1

HCID 944Nitric AcidSolvent

Conditions

Temperature
80 °C

Procedure

L-(+)-Leucine (10 g, 0.076 moles) is mixed with 24 mL of concentrated HCl and 10 mL of concentrated HNO3 with the addition of 2 g of urea and subsequently heated for 1 hour at 80° C. and then for 1 hour at 50° C. on a water bath (complete dissolution of the acid with heavy foaming). After cooling, the solution is extracted with ether several times, the ether extract is washed with water and dried over calcium chloride, the solvent is distilled off in a rotary evaporator and the residue is fractionally distilled under vacuum.

Workup

  1. dissolutionfor 1 hour at 50° C. on a water bath (complete dissolution of the acid with heavy foaming)
  2. temperatureAfter cooling
  3. extractionthe solution is extracted with ether several times
  4. extractionthe ether extract
  5. washis washed with water
  6. dry with materialdried over calcium chloride
  7. distillationthe solvent is distilled off in a rotary evaporator
  8. distillationthe residue is fractionally distilled under vacuum

Sources & evidence

ORD record
ord-2c00c676e0c1468a958b90074c5ddc6b
Source dataset
uspto-grants-1990_10
Patent number
US04961876

Reaction notes

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