Water → N-(3-acetylthio-2-acetylthiomethylpropionyl)-N-(5,6-dimethoxy-1-indanyl)glycine

HRID 1248063Notes

Reaction equation

HRID 1248063 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][C:11]=1[O:12][CH3:13])[CH:8]([NH:14][CH2:15][C:16]([OH:18])=[O:17])[CH2:7][CH2:6]2.[C:19]([S:22][CH2:23][CH:24]([CH2:28][S:29][C:30](=[O:32])[CH3:31])[C:25](Cl)=[O:26])(=[O:21])[CH3:20].O>CC(N(C)C)=O>[C:19]([S:22][CH2:23][CH:24]([CH2:28][S:29][C:30](=[O:32])[CH3:31])[C:25]([N:14]([CH:8]1[C:9]2[C:5](=[CH:4][C:3]([O:2][CH3:1])=[C:11]([O:12][CH3:13])[CH:10]=2)[CH2:6][CH2:7]1)[CH2:15][C:16]([OH:18])=[O:17])=[O:26])(=[O:21])[CH3:20]

Participants

5

Reactant 3

HCID 962WaterHCID 129261603-Acetylthio-2-acetylthiomethylpropionyl chlorideHCID 13472326N-(5,6-dimethoxy-1-indanyl)glycine

Product 1

HCID 13472311N-(3-acetylthio-2-acetylthiomethylpropionyl)-N-(5,6-dimethoxy-1-indanyl)glycineYield 45.5%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

N-(5,6-Dimethoxy-1-indanyl)glycine (4.0 g) is suspended in 40 ml of dimethylacetamide, then 4.4 g of 3-acetylthio-2-acetylthiomethylpropionyl chloride is added dropwise with stirring at room temperature, and the mixture is stirred at room temperature for 2 hours. The reaction mixture is poured into 400 ml of water and extracted with 300 ml of ethyl acetate. The extract is washed with 30 ml of 10% hydrochloric acid and with water, and dried. After ethyl acetate is distilled off under reduced pressure, ethyl ether is added to the residue and the mixture is allowed to stand at room temperature. The resulting crystalline precipitates are collected by filtration to give 3.4 g of N-(3-acetylthio-2-acetylthiomethylpropionyl)-N-(5,6-dimethoxy-1-indanyl)glycine as colorless needles melting at 140°-143° C.

Workup

  1. stirringthe mixture is stirred at room temperature for 2 hours
  2. extractionextracted with 300 ml of ethyl acetate
  3. washThe extract is washed with 30 ml of 10% hydrochloric acid and with water
  4. customdried
  5. distillationAfter ethyl acetate is distilled off under reduced pressure, ethyl ether
  6. additionis added to the residue
  7. customto stand at room temperature
  8. customThe resulting crystalline precipitates
  9. filtrationare collected by filtration

Sources & evidence

ORD record
ord-f0c6b678a08148208007fa6a8bb26add
Source dataset
uspto-grants-1985_06
Patent number
US04521607

Reaction notes

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