Acetone → HCID 12804608, compound

HRID 223301Notes

Reaction equation

HRID 223301 reaction equation
[CH3:1][C:2]([CH3:4])=O.OS(O)(=O)=O.[O:10]=[Cr](=O)=O.ClC(Cl)(Cl)CO[C:18]([NH:20][C@@H:21]1[CH2:40][C@@:39]2([CH3:41])[C@@H:32]([CH2:33][CH2:34][C@@H]2C(=O)C)[C@H:31]2[C@H:22]1[C@:23]1([CH3:51])[C@H:28]([CH2:29][CH2:30]2)[CH2:27][C@H:26]([O:42]C(OCC(Cl)(Cl)Cl)=O)[CH2:25][CH2:24]1)=O.N.C[CH2:56][O:57][CH2:58][CH3:59].[CH3:60][C:61](C)=O>O>[CH:18]1([NH:20][C@@H:21]2[CH2:40][C@@:39]3([CH3:41])[C@@H:32]([CH2:33][CH2:34][C@@H:59]3[C:58]([O:57][CH3:56])=[O:10])[C@H:31]3[C@H:22]2[C@:23]2([CH3:51])[C@@H:28]([CH2:29][CH2:30]3)[CH2:27][C:26](=[O:42])[CH2:25][CH2:24]2)[CH2:61][CH2:60][CH2:4][CH2:2][CH2:1]1

Participants

7

Reactant 5

HCID 180AcetoneHCID 222AmmoniaHCID 3283Diethyl EtherHCID 12804704HCID 12804704, compoundHCID 131709961Jones' reagent

Product 1

HCID 12804608HCID 12804608, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Jones reagent was added dropwise to a stirred solution of the product of Preparation 11 (3.095 g) in acetone (225 ml) until the reagent colour was not discharged. After 2.5 h the mixture was diluted with water (300 ml) and brought to pH 10 with 0.88 NH3 solution. The mixture was shaken with ether (250 ml) and the total liquid was filtered. The aqueous phase was separated and extracted with ether (250 ml) and the combined organic phase was washed with water (×2), dried and evaporated to leave an oil (2.099 g). A sample (0.5 g) was purified by preparative t.l.c. using CHCl3 :MeOH (19:1) and crystallised from petrol to give the total compound m.p. 91°-93° C., [α]D -14°.

Workup

  1. filtrationthe total liquid was filtered
  2. customThe aqueous phase was separated
  3. extractionextracted with ether (250 ml)
  4. washthe combined organic phase was washed with water (×2)
  5. customdried
  6. customevaporated

Sources & evidence

ORD record
ord-ab7500d63c574cc8ac7d62e9c281d3b5
Source dataset
uspto-grants-1982_10
Patent number
US04352798

Reaction notes

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