Acetyl chloride → HCID 18473942, compound

HRID 564856Notes

Reaction equation

HRID 564856 reaction equation
[NH2:1][C:2]1[O:3][CH:4]([CH:8]([C:10]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[NH:12][CH:11]=2)[CH3:9])[C:5](=[O:7])[N:6]=1.[O:19]1[CH2:23][CH2:22]CC1.C(N(CC)CC)C.[C:31](Cl)(=[O:33])[CH3:32]>O>[C:31]([N:1]([C:23](=[O:19])[CH3:22])[C:2]1[O:3][CH:4]([CH:8]([C:10]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[NH:12][CH:11]=2)[CH3:9])[C:5](=[O:7])[N:6]=1)(=[O:33])[CH3:32]

Participants

6

Reactant 4

HCID 6367Acetyl chloride2×HCID 8028TetrahydrofuranHCID 8471Triethylamine2×HCID 13749522HCID 13749522, compound

Product 1

HCID 18473942HCID 18473942, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

2-amino-5-[1-(indol-3-yl)ethyl]-2-oxazolin-4-one (300 mg) was dissolved into tetrahydrofuran (2 ml). Triethylamine (344 μl) and acetyl chloride (123 μl) were added under ice cooling. The mixture was stirred for 2 hours at 0° C. Triethylamine (344 μl) and acetyl chloride (123 μl) were added again. The whole was further stirred for 2 hours. To the reaction mixture was added water and the whole was extracted with ethyl acetate. The extract was washed with brine and dried over magnesium sulfate. Concentration of the solution gave a residue, which was subjected to silica gel chromatography. The eluent with hexane-acetone (1:1) was collected and concentrated to provide the titled compound (40 mg).

Workup

  1. stirringThe whole was further stirred for 2 hours
  2. extractionthe whole was extracted with ethyl acetate
  3. washThe extract was washed with brine
  4. dry with materialdried over magnesium sulfate
  5. customConcentration of the solution gave a residue, which
  6. customThe eluent with hexane-acetone (1:1) was collected
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-e90447b473864ae984b3d4535fc5bd72
Source dataset
uspto-grants-2001_01
Patent number
US06169102A

Reaction notes

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