Water → N-(3-acetylthio-2-methylpropionyl)-N-(4-methoxy-1-indanyl)glycine ethyl ester

HRID 1248058Notes

Reaction equation

HRID 1248058 reaction equation
[CH2:1]([O:3][C:4](=[O:18])[CH2:5][NH:6][CH:7]1[C:15]2[C:10](=[C:11]([O:16][CH3:17])[CH:12]=[CH:13][CH:14]=2)[CH2:9][CH2:8]1)[CH3:2].[C:19]([S:22][CH2:23][CH:24]([CH3:28])[C:25](Cl)=[O:26])(=[O:21])[CH3:20].O>CC(N(C)C)=O>[CH2:1]([O:3][C:4](=[O:18])[CH2:5][N:6]([C:25](=[O:26])[CH:24]([CH3:28])[CH2:23][S:22][C:19](=[O:21])[CH3:20])[CH:7]1[C:15]2[C:10](=[C:11]([O:16][CH3:17])[CH:12]=[CH:13][CH:14]=2)[CH2:9][CH2:8]1)[CH3:2]

Participants

5

Reactant 3

HCID 962WaterHCID 103458Ethanethioic acid, S-(3-chloro-2-methyl-3-oxopropyl) esterHCID 13472328HCID 13472328, compound

Product 1

HCID 20280801N-(3-acetylthio-2-methylpropionyl)-N-(4-methoxy-1-indanyl)glycine ethyl esterYield 67.6%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

N-(4-Methoxy-1-indanyl)glycine ethyl ester (3.0 g) is dissolved in 30 ml of dimethylacetamide, then 3.3 g of 3-acetylthio-2-methylpropionyl 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 200 ml of water, and extracted with ethyl acetate. The extract is washed with 10 ml of 10% hydrochloric acid and with water and dried, and ethyl acetate is distilled off under reduced pressure. The residue is purified by subjecting to silica gel column chromatography eluted with acetone-benzene (1:20), to give 3.2 g of N-(3-acetylthio-2-methylpropionyl)-N-(4-methoxy-1-indanyl)glycine ethyl ester as a colorless oil.

Workup

  1. stirringthe mixture is stirred at room temperature for 2 hours
  2. extractionextracted with ethyl acetate
  3. washThe extract is washed with 10 ml of 10% hydrochloric acid and with water
  4. customdried
  5. distillationethyl acetate is distilled off under reduced pressure
  6. customThe residue is purified
  7. washeluted with acetone-benzene (1:20)

Sources & evidence

ORD record
ord-4c07a100d259426eba49ad147e3896dd
Source dataset
uspto-grants-1985_06
Patent number
US04521607

Reaction notes

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