Water → HCID 19889967, compound

HRID 653693Notes

Reaction equation

HRID 653693 reaction equation
[CH3:1][C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]=1[N:12]([CH:17]1[CH2:21][CH2:20][O:19][C:18]1=[O:22])[C:13](=[O:16])[CH2:14]Cl.[C:23]([O-:26])(=[O:25])[CH3:24].[Na+].O>CN(C)C=O>[CH3:1][C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]=1[N:12]([CH:17]1[CH2:21][CH2:20][O:19][C:18]1=[O:22])[C:13](=[O:16])[CH2:14][O:26][C:23](=[O:25])[CH3:24]

Participants

5

Reactant 3

HCID 962WaterHCID 517045Sodium AcetateHCID 12796022HCID 12796022, compound

Product 1

HCID 19889967HCID 19889967, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 18.2 g of N-(2-methylnaphthyl)-N-(2-oxo-tetrahydrofuran-3-yl)-N-chloroacetyl-amine, 11.5 g of anhydrous sodium acetate and 0.1 g of KJ in 70 ml of dimethylformamide (DMF) is heated at 110° for 16 hours. The reaction mixture is afterwards cooled to room temperature, poured into 200 ml of water and extracted three times with 50 ml of ethyl acetate each time. The combined extracts are washed with 50 ml of water, dried over sodium sulfate, filtered and then concentrated by evaporation. The dark-brown oil remaining is purified through silica gel 60 (particle size 0.06-0.2 mm) using chloroform/diethyl ether (1:1) as the eluant. The last 10 of 12 fractions are combined and the eluant is evaporated off. The diastereoisomeric mixture of the compound No. 19 which remains solidifies on cooling, m.p. 50°-70°.

Workup

  1. temperatureis heated at 110° for 16 hours
  2. extractionextracted three times with 50 ml of ethyl acetate each time
  3. washThe combined extracts are washed with 50 ml of water
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated by evaporation
  7. customThe dark-brown oil remaining is purified through silica gel 60 (particle size 0.06-0.2 mm)
  8. customthe eluant is evaporated off
  9. additionThe diastereoisomeric mixture of the compound No
  10. temperatureon cooling

Sources & evidence

ORD record
ord-d80a0d93fecc42589fd29080600a8ef4
Source dataset
uspto-grants-1992_07
Patent number
US05128371

Reaction notes

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