Jones' reagent → HCID 178454997, compound

HRID 1728473Notes

Reaction equation

HRID 1728473 reaction equation
[CH:1]([C@@H:3]1[N:6]([Si:7]([C:10]([CH3:13])([CH3:12])[CH3:11])([CH3:9])[CH3:8])[C:5](=[O:14])[C@H:4]1[CH2:15][CH2:16][CH2:17][NH:18][C:19]([NH:31][C:32]([O:34][CH2:35][C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1)=[O:33])=[N:20][C:21]([O:23][CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)=[O:22])=[O:2].[CH3:42][C:43]([CH3:45])=[O:44].OS(O)(=O)=O.O=[Cr](=O)=O>CC(C)=O>[C:43]1([CH:45]=[CH:1][C@@H:3]2[N:6]([Si:7]([C:10]([CH3:12])([CH3:11])[CH3:13])([CH3:8])[CH3:9])[C:5](=[O:14])[C@H:4]2[CH2:15][CH2:16][CH2:17][NH:18][C:19]([NH:31][C:32]([O:34][CH2:35][C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)=[O:33])=[N:20][C:21]([O:23][CH2:24][C:25]2[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=2)=[O:22])[CH:5]=[CH:4][CH:3]=[CH:1][CH:42]=1.[C:1]([C@@H:3]1[NH:6][C:5](=[O:14])[C@H:4]1[CH2:15][CH2:16][CH2:17][NH:18][C:19]([NH:31][C:32]([O:34][CH2:35][C:36]1[CH:37]=[CH:38][CH:39]=[CH:40][CH:41]=1)=[O:33])=[N:20][C:21]([O:23][CH2:24][C:25]1[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=1)=[O:22])([OH:2])=[O:44]

Participants

5

Reactant 2

HCID 131709961Jones' reagentHCID 178454999HCID 178454999, compound

Product 2

HCID 178454997HCID 178454997, compoundHCID 178523911HCID 178523911, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent2×

Procedure

The aldehyde 5a prepared in Step A was dissolved in acetone (75 mL). Freshly prepared Jones reagent was added dropwise to the acetone solution, maintaining the temperature between 20°-25° C., until the TLC indicated the disappearance of the starting aldehyde. The resultant suspension was concentrated to half of its original volume and partitioned between EtOAc and H2O. The organic phase was dried (Na2SO4) and concentrated. The residual solid was recrystallized from EtOAc/hexane to afford 8.8 g (54% from 4a) of the title compound as a greenish solid, mp 172°-173° C.

Workup

  1. temperaturemaintaining the temperature between 20°-25° C.
  2. concentrationThe resultant suspension was concentrated to half of its original volume
  3. custompartitioned between EtOAc and H2O
  4. dry with materialThe organic phase was dried (Na2SO4)
  5. concentrationconcentrated
  6. customThe residual solid was recrystallized from EtOAc/hexane

Sources & evidence

ORD record
ord-7162e0425a0a49bba33bfec8ad344cfd
Source dataset
uspto-grants-1994_07
Patent number
US05326863

Reaction notes

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