Sulfuric Acid → HCID 178421603, compound

HRID 428924Notes

Reaction equation

HRID 428924 reaction equation
[CH3:1][C:2]1([C:18]2[CH:23]=[CH:22][CH:21]=[C:20]([C:24]3[N:25]=[N:26][NH:27][C:28]=3[Si](C)(C)C)[CH:19]=2)[CH:7]2[CH:3]1[CH2:4][N:5]([CH2:9][CH2:10][CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[C:6]2=[O:8].[F-].[K+].S(=O)(=O)(O)O>C(O)C>[CH3:1][C:2]1([C:18]2[CH:23]=[CH:22][CH:21]=[C:20]([C:24]3[NH:25][N:26]=[N:27][CH:28]=3)[CH:19]=2)[CH:7]2[CH:3]1[CH2:4][N:5]([CH2:9][CH2:10][CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[C:6]2=[O:8]

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 522689Potassium FluorideHCID 178421607HCID 178421607, compound

Product 1

HCID 178421603HCID 178421603, compoundYield 66.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 6-methyl-3-(3-phenylpropyl)-6-{3-[5-(trimethylsilyl)-1H-1,2,3-triazol-4-yl]phenyl}-3-azabicyclo[3.1.0]hexan-2-one (Preparation 38, 58.0 mg, 0.13 mmol) in ethanol (2 ml) was added potassium fluoride (8.3 mg, 0.14 mmol) and a drop of concentrated sulphuric acid. The mixture was heated at reflux for 4 hours and then stirred at room temperature for 16 hours. The solvent was removed in vacuo and the crude residue was absorbed onto silica. This material was then purified by silica column chromatography eluting first with hexane:ethyl acetate (1:1) and then increasing gradually to neat ethyl acetate. The desired title compound (32 mg, 66%) was isolated as a colourless oil.

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 4 hours
  3. customThe solvent was removed in vacuo
  4. customthe crude residue was absorbed onto silica
  5. customThis material was then purified by silica column chromatography
  6. washeluting first with hexane:ethyl acetate (1:1)
  7. temperatureincreasing gradually to neat ethyl acetate

Sources & evidence

ORD record
ord-7d8e7068b16644b7b69be5c1d59c372b
Source dataset
uspto-grants-2001_11
Patent number
US06313312B1

Reaction notes

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