Water → HCID 13472306, compound

HRID 1248055Notes

Reaction equation

HRID 1248055 reaction equation
[CH3:1][O:2][C:3]1[CH:11]=[C:10]2[C:6]([CH2:7][CH2:8][CH:9]2[NH:12][CH2:13][C:14]([OH:16])=[O:15])=[CH:5][CH:4]=1.[C:17]([S:20][CH2:21][CH:22]([CH3:26])[C:23](Cl)=[O:24])(=[O:19])[CH3:18].O>CC(N(C)C)=O>[C:17]([S:20][CH2:21][CH:22]([CH3:26])[C:23]([N:12]([CH:9]1[C:10]2[C:6](=[CH:5][CH:4]=[C:3]([O:2][CH3:1])[CH:11]=2)[CH2:7][CH2:8]1)[CH2:13][C:14]([OH:16])=[O:15])=[O:24])(=[O:19])[CH3:18]

Participants

5

Reactant 3

HCID 962WaterHCID 103458Ethanethioic acid, S-(3-chloro-2-methyl-3-oxopropyl) esterHCID 12851967HCID 12851967, compound

Product 1

HCID 13472306HCID 13472306, compoundYield 54.5%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

N-(6-Methoxy-1-indanyl)glycine (2.0 g) is suspended in 20 ml of dimethylacetamide, then 2.2 g of 3-acetylthio-2-methylpropionyl chloride is added dropwise with stirring at room temperature, and thereafter stirring is continued at room temperature for 2 hours. The reaction mixture is poured into 200 ml of water, and extracted with 200 ml of ethyl acetate. The extract is washed with 20 ml of 10% hydrochloric acid and with water, and dried over anhydrous sodium sulfate. After ethyl acetate is distilled off under reduced pressure, the residue is subjected to silica gel column chromatography, eluted with acetone-benzene (1:9). The oily substance obtained is crystallized from an ethyl ether-petroleum ether mixture, to give 1.8 g of N-(3-acetylthio-2-methylpropionyl)-N-(6-methoxy-1-indanyl)glycine, colorless needles showing a melting point of 106°-110° C.

Workup

  1. stirringstirring
  2. extractionextracted with 200 ml of ethyl acetate
  3. washThe extract is washed with 20 ml of 10% hydrochloric acid and with water
  4. dry with materialdried over anhydrous sodium sulfate
  5. distillationAfter ethyl acetate is distilled off under reduced pressure
  6. washeluted with acetone-benzene (1:9)
  7. customThe oily substance obtained
  8. customis crystallized from an ethyl ether-petroleum ether mixture

Sources & evidence

ORD record
ord-c96656f2e47345b3911cdb5dec495a18
Source dataset
uspto-grants-1985_06
Patent number
US04521607

Reaction notes

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