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

HRID 2309050Notes

Reaction equation

HRID 2309050 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 organic 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 organic 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-35eddacf52704ca5b5e2997015c2a36c
Source dataset
uspto-grants-1987_09
Patent number
US04692458

Reaction notes

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