L-Valine → HCID 22859213, compound

HRID 1252816Notes

Reaction equation

HRID 1252816 reaction equation
[NH2:1][C@H:2]([C:6]([OH:8])=[O:7])[CH:3]([CH3:5])[CH3:4].C(=O)([O-])[O-].[Na+].[Na+].[C:15]([S:18][CH2:19][CH:20]([CH3:24])[C:21](Cl)=[O:22])(=[O:17])[CH3:16]>O>[C:15]([S:18][CH2:19][CH:20]([CH3:24])[C:21]([NH:1][C@H:2]([C:6]([OH:8])=[O:7])[CH:3]([CH3:5])[CH3:4])=[O:22])(=[O:17])[CH3:16]

Participants

5

Reactant 3

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

Product 1

HCID 22859213HCID 22859213, compoundYield 97.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

L-valine (88 g) and sodium carbonate (40 g) are dissolved in water (1 l.) 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 Step (b), Example 49.

Workup

  1. temperaturethe solution is chilled in an ice bath with vigorous stirring
  2. extractionthe 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

Sources & evidence

ORD record
ord-df4d784d46d844f3a3fa626ff07d7c60
Source dataset
uspto-grants-1988_05
Patent number
US04745124

Reaction notes

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