Jones' reagent → HCID 178473979, compound

HRID 1728488Notes

Reaction equation

HRID 1728488 reaction equation
[CH:1]([C@@H:3]1[N:6]([C:7](=[O:9])[CH3:8])[C:5](=[O:10])[C@H:4]1[CH2:11][CH2:12][CH2:13][NH:14][C:15]([NH:27][C:28]([O:30][CH2:31][C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)=[O:29])=[N:16][C:17]([O:19][CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)=[O:18])=[O:2].CC(C)=[O:40].OS(O)(=O)=O.O=[Cr](=O)=O>CC(C)=O>[C:1]([C@@H:3]1[N:6]([C:7](=[O:9])[CH3:8])[C:5](=[O:10])[C@H:4]1[CH2:11][CH2:12][CH2:13][NH:14][C:15]([NH:27][C:28]([O:30][CH2:31][C:32]1[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=1)=[O:29])=[N:16][C:17]([O:19][CH2:20][C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1)=[O:18])([OH:40])=[O:2]

Participants

4

Reactant 2

HCID 131709961Jones' reagentHCID 178473976HCID 178473976, compound

Product 1

HCID 178473979HCID 178473979, compoundYield 66%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To an acetone solution of compound 28 (3.5 g, 6.8 mmol) was added freshly prepared Jones reagent dropwise until TLC indicated the disappearance of the starting material. The acetone layer was separated, and the residue was washed with a fresh portion of acetone. Two acetone portions were combined and concentrated. The residue was purified by silica gel chromatography (EtOAc:MeOH/99:1) to afford 2.4 g (66%) of the title product.

Workup

  1. customThe acetone layer was separated
  2. washthe residue was washed with a fresh portion of acetone
  3. concentrationconcentrated
  4. customThe residue was purified by silica gel chromatography (EtOAc:MeOH/99:1)

Sources & evidence

ORD record
ord-c41799c6a56e4b76971aa1360d8f07a1
Source dataset
uspto-grants-1994_07
Patent number
US05326863

Reaction notes

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