Sodium Hydroxide → HCID 23047368, compound

HRID 2107058Notes

Reaction equation

HRID 2107058 reaction equation
[CH2:1]([O:8][C:9]1[CH:21]=[CH:20][CH:19]=[C:18]2[C:10]=1[C:11]1[C:12]([CH2:35][O:36][CH3:37])=[C:13]([CH:32]=[N:33][OH:34])[N:14]=[CH:15][C:16]=1[N:17]2S(C1C=CC(C)=CC=1)(=O)=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.ClN1C(=O)C[CH2:41][C:40]1=O.C[Si](C#C)(C)C.[OH-].[Na+]>C(Cl)Cl.O.C(N(CC)CC)C>[CH2:1]([O:8][C:9]1[CH:21]=[CH:20][CH:19]=[C:18]2[C:10]=1[C:11]1[C:12]([CH2:35][O:36][CH3:37])=[C:13]([C:32]3[CH:41]=[CH:40][O:34][N:33]=3)[N:14]=[CH:15][C:16]=1[NH:17]2)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

8

Reactant 4

HCID 14798Sodium HydroxideHCID 31398ChlorosuccinimideHCID 66111TrimethylsilylacetyleneHCID 136364614HCID 136364614, compound

Product 1

HCID 23047368HCID 23047368, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 8471TriethylamineSolvent

Procedure

103 mg of 5-benzyloxy-4-methoxymethyl-9-tosyl-β-carboline-3-carbaldehyde oxime is combined in 5 ml of methylene chloride with 22 mg of N-chlorosuccinimide and agitated for one hour at room temperature. Subsequently 30 mg of trimethylsilylacetylene and 0.13 ml of triethylamine are added and the mixture stirred for 2 hours at room temperature. The mixture is then combined with 1 ml of 1N sodium hydroxide solution and agitated for one hour at room temperature, poured on 25 ml of water, extracted with 25 ml of methylene chloride, and the organic phase is dried, filtered, and concentrated. The residue is refluxed for 1.5 hours in 15 ml of methanol with 54 mg of sodium methylate. After concentration, the mixture is taken up in 25 ml of water and extracted with ethyl acetate. After drying and filtration, the organic phase is concentrated and the residue is chromatographed over silica gel with toluene+ethyl acetate in a ratio of 1:1 as the eluent.

Workup

  1. stirringthe mixture stirred for 2 hours at room temperature
  2. stirringagitated for one hour at room temperature
  3. extractionextracted with 25 ml of methylene chloride
  4. customthe organic phase is dried
  5. filtrationfiltered
  6. concentrationconcentrated
  7. temperatureThe residue is refluxed for 1.5 hours in 15 ml of methanol with 54 mg of sodium methylate
  8. concentrationAfter concentration
  9. extractionextracted with ethyl acetate
  10. customAfter drying
  11. filtrationfiltration
  12. concentrationthe organic phase is concentrated
  13. customthe residue is chromatographed over silica gel with toluene+ethyl acetate in a ratio of 1:1 as the eluent

Sources & evidence

ORD record
ord-27f1b42383c04cb3a039c89f7c3a58d3
Source dataset
uspto-grants-1990_06
Patent number
US04933345

Reaction notes

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