L-Valine → N-(2-Methyl-3-sulfanylpropanoyl)-L-valine

HRID 1762514Notes

Reaction equation

HRID 1762514 reaction equation
N[C@H](C(O)=O)C(C)C.C(=O)([O-])[O-].[Na+].[Na+].C(SCC(C)C(Cl)=O)(=O)C.C([S:28][CH2:29][CH:30]([CH3:41])[C:31]([NH:33][C@H:34]([C:38]([OH:40])=[O:39])[CH:35]([CH3:37])[CH3:36])=[O:32])(=O)C>O>[SH:28][CH2:29][CH:30]([CH3:41])[C:31]([NH:33][C@H:34]([C:38]([OH:40])=[O:39])[CH:35]([CH3:36])[CH3:37])=[O:32]

Participants

6

Reactant 4

HCID 6287L-ValineHCID 10340Sodium Carbonate2×HCID 103458Ethanethioic acid, S-(3-chloro-2-methyl-3-oxopropyl) esterHCID 22859213HCID 22859213, compound

Product 1

HCID 22859220N-(2-Methyl-3-sulfanylpropanoyl)-L-valine

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

L-valine (88 g.) and sodium carbonate (40 g.) are dissolved in water (11.) and the solution is chilled in an ice bath with vigorous stirring. 3-Acetylthio-2-methylpropanoyl chloride (135 g.) and a solution of sodium carbonate (120 g.) in 500 ml. of water are added in five equal portions over a 15 minute period. After 1.5 hours the reaction mixture is extracted with ethyl acetate, the aqueous phase is acidified with concentrated hydrochloric acid and extracted with ethyl acetate. The oranic phase is washed with water, dried over magnesium sulfate and concentrated to dryness to yield 190 g. of N-(3-acetylthio-2-methylpropanoyl)-L-valine. The named product is obtained by following the procedure of Example 50.

Workup

  1. temperaturethe solution is chilled in an ice bath with vigorous stirring
  2. extractionAfter 1.5 hours the reaction mixture is extracted with ethyl acetate
  3. extractionextracted with ethyl acetate
  4. washThe oranic phase is washed with water
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated to dryness
  7. customto yield 190 g
  8. customThe named product is obtained

Sources & evidence

ORD record
ord-c08a20cde252456e9bd205544bb5ac6f
Source dataset
uspto-grants-1989_05
Patent number
US04833152

Reaction notes

Loading…