HCID 70043459, compound → HCID 70045244, compound

HRID 1198497Notes

Reaction equation

HRID 1198497 reaction equation
[C:1]([N:8]1[CH2:13][CH2:12][CH:11]([CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][OH:19])[CH2:10][CH2:9]1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].[NH:20]1[CH2:24][CH2:23][CH2:22][C:21]1=[O:25].CC(C)=O.OS(O)(=O)=O.O=[Cr](=O)=O>CC(C)=O.C([O-])(O)=O.[Na+]>[C:1]([N:8]1[CH2:13][CH2:12][CH:11]([CH2:14][CH2:15][CH2:16][CH2:17][C:18]([OH:25])=[O:19])[CH2:10][CH2:9]1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].[NH:20]1[CH2:24][CH2:23][CH2:22][C:21]1=[O:25]

Participants

5

Reactant 2

HCID 70043459HCID 70043459, compoundHCID 131709961Jones' reagent

Product 1

HCID 70045244HCID 70045244, compound

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 516892Sodium BicarbonateSolvent

Procedure

A solution of 95 (1.14 mmol) in acetone (5 ml) was cooled to -15° and treated with Jones reagent until the color remained amber/brown. The reaction mixture was diluted with saturated NaHCO3 solution to pH 9 and this was extracted with EtOAc. The aqueous phase was acidified to pH 3 with KHSO4 solution and extracted with several portions of EtOAc. The combined organic extracts were dried (MgSO4) and the, solvent removed to give 96. Rf 0.3 (silica gel, 9/1/1 CH2Cl2 /MeOH/HOAc).

Workup

  1. extractionthis was extracted with EtOAc
  2. extractionextracted with several portions of EtOAc
  3. dry with materialThe combined organic extracts were dried (MgSO4)
  4. customthe, solvent removed

Sources & evidence

ORD record
ord-4d61c613953942fd85686d3b579c8932
Source dataset
uspto-grants-1994_01
Patent number
US05281585

Reaction notes

Loading…