Sodium Carbonate → 1-[3-acetylthio-2-(methylthiomethyl)propanoyl]-L-proline

HRID 46926Notes

Reaction equation

HRID 46926 reaction equation
[NH:1]1[CH2:8][CH2:7][CH2:6][C@H:2]1[C:3]([OH:5])=[O:4].C(=O)([O-])[O-].[Na+].[Na+].[C:15]([S:18][CH2:19][CH:20]([CH2:24][S:25][CH3:26])[C:21](Cl)=[O:22])(=[O:17])[CH3:16].C(SCC(CSC)C(O)=O)(=O)C.S(Cl)(Cl)=O>O>[C:15]([S:18][CH2:19][CH:20]([CH2:24][S:25][CH3:26])[C:21]([N:1]1[CH2:8][CH2:7][CH2:6][C@H:2]1[C:3]([OH:5])=[O:4])=[O:22])(=[O:17])[CH3:16]

Participants

7

Reactant 5

HCID 10340Sodium CarbonateHCID 24386Thionyl ChlorideHCID 145742L-ProlineHCID 141814883-(Acetylthio)-2-(methylthiomethyl)propanoic acidHCID 543729953-(Acetylthio)-2-(methylthiomethyl)propanoic acid chloride

Product 1

HCID 539119981-[3-acetylthio-2-(methylthiomethyl)propanoyl]-L-proline

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of L-proline (1.44 g.) and sodium carbonate (2.7 g.) in water (25 ml.) in an ice bath, 3-(acetylthio)-2-(methylthiomethyl)propanoic acid chloride (prepared from the acid of Example 15 with thionyl chloride) (3.6 g.) is added, and the mixture is vigorously stirred at room temperature for two hours. After extraction with ethyl acetate, the aqueous layer is acidified and extracted with ethyl acetate. The organic layer is dried and concentrated to dryness in vacuo to give 1-[3-(acetylthio)-2-(methylthiomethyl)propanoyl]-L-proline.

Workup

  1. additionis added
  2. extractionAfter extraction with ethyl acetate
  3. extractionextracted with ethyl acetate
  4. customThe organic layer is dried
  5. concentrationconcentrated to dryness in vacuo

Sources & evidence

ORD record
ord-ba9ee55792e54518bc9a68688d110123
Source dataset
uspto-grants-1979_11
Patent number
US04175199

Reaction notes

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