Ethanol → HCID 178482438, compound

HRID 564854Notes

Reaction equation

HRID 564854 reaction equation
[Na].C(O)C.[Cl:5][C:6]1[CH:14]=[CH:13][CH:12]=[C:11]2[C:7]=1[C:8]([C@@H:15]([CH3:23])[C@H:16]([OH:22])[C:17](OCC)=[O:18])=[CH:9][NH:10]2.Br.[CH3:25][NH:26][C:27](NC)=[NH:28]>O>[Cl:5][C:6]1[CH:14]=[CH:13][CH:12]=[C:11]2[C:7]=1[C:8]([CH:15]([CH:16]1[O:22][C:27]([NH:26][CH3:25])=[N:28][C:17]1=[O:18])[CH3:23])=[CH:9][NH:10]2

Participants

6

Reactant 4

HCID 702EthanolHCID 5360545SodiumHCID 86756194HCID 86756194, compoundHCID 178419593HCID 178419593, compound

Product 1

HCID 178482438HCID 178482438, compoundYield 12.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Sodium (100 mg) was dissolved into ethanol (5 ml). Ethyl (2S*,3R*)-3-(4-chloroindol-3-yl)-2-hydroxybutyrate (200 mg) and N,N′-dimethyl guanidine hydrogen bromide (143 mg) were added. The whole was refluxed for 16 hours. To the reaction mixture was added water and 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. Elution with hexane-acetone (1:1) provided the titled compound (25 mg).

Workup

  1. temperatureThe whole was refluxed for 16 hours
  2. extractionextracted 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. washElution with hexane-acetone (1:1)

Sources & evidence

ORD record
ord-8c0c1bd574e14284918cd7069366ddc8
Source dataset
uspto-grants-2001_01
Patent number
US06169102A

Reaction notes

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