Potassium Permanganate → HCID 21517621, compound

HRID 1283693Notes

Reaction equation

HRID 1283693 reaction equation
C(OC(C([N:15]1[CH:18]([S:19][CH2:20][C:21]#[C:22][CH2:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[CH:17]([NH:30][C:31]([C:44]2[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=2)([C:38]2[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=2)[C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[C:16]1=[O:50])=C(C)C)=O)C1C=CC=CC=1.[Mn]([O-])(=O)(=O)=O.[K+]>N1C=CC=CC=1.O.C(OCC)(=O)C.S(=O)=O.[O-2].[O-2].[Mn+4]>[C:24]1([CH2:23][C:22]#[C:21][CH2:20][S:19][CH:18]2[NH:15][C:16](=[O:50])[CH:17]2[NH:30][C:31]([C:44]2[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=2)([C:38]2[CH:39]=[CH:40][CH:41]=[CH:42][CH:43]=2)[C:32]2[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=2)[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1

Participants

8

Reactant 2

HCID 516875Potassium PermanganateHCID 21517647HCID 21517647, compound

Product 1

HCID 21517621HCID 21517621, compoundYield 22%

Reagents, catalysts & solvents 5

HCID 178418406HCID 178418406, compoundCatalystHCID 962WaterSolvent2×HCID 1049PyridineSolventHCID 1119Sulfur DioxideSolventHCID 8857Ethyl AcetateSolvent

Procedure

1-(1-Benzyloxycarbonyl-2-methyl-1-propenyl)-3-(triphenylmethylamino)-4-(4-phenylbut-2-ynylthio)azetidin-2-one (5.40g) was dissolved in a mixture of pyridine (60ml) and water (6ml). The stirred mixture was cooled in an ice-salt bath and finely powdered potassium permanganate (2.30g) was added. The cooled mixture was stirred for a further 1.5 hours. The mixture was diluted with ethyl acetate (100ml) and water (10ml) and sulphur dioxide was passed until the manganese dioxide had dissolved. The organic layer was separated and washed successively with sodium bicarbonate solution, brine, N.hydrochloric acid, and brine The dried (MgSO4) organic layer was evaporated to give a crude gum (4.8g). The crude gum was chromatographed on silica gel eluting with ethyl acetate/petroleum ether mixtures to give 4-(4-phenylbut-2-ynylthio)-3-triphenylmethylaminoazetidin-2-one as a crystalline solid (0.852g, 22%). Recrystallisation of the product gave a colourless crystalline solid, MP=145°-6°C.

Workup

  1. temperatureThe stirred mixture was cooled in an ice-salt bath
  2. dissolutionhad dissolved
  3. customThe organic layer was separated
  4. washwashed successively with sodium bicarbonate solution, brine, N
  5. dry with materialhydrochloric acid, and brine The dried (MgSO4) organic layer
  6. customwas evaporated
  7. customto give a crude gum (4.8g)
  8. customThe crude gum was chromatographed on silica gel eluting with ethyl acetate/petroleum ether

Sources & evidence

ORD record
ord-3d92891f8586481ca1885718a3bf8f9b
Source dataset
uspto-grants-1976_08
Patent number
US03975383

Reaction notes

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