HCID 22901975, compound → HCID 22902007, compound

HRID 1768630Notes

Reaction equation

HRID 1768630 reaction equation
[CH3:1][C:2]([NH:5][S:6]([C:9]1[S:17][C:16]2[S:15](=[O:19])(=[O:18])[N:14]([CH2:20][CH2:21][CH2:22][CH2:23][O:24][CH3:25])[CH2:13][CH:12]([OH:26])[C:11]=2[CH:10]=1)(=[O:8])=[O:7])([CH3:4])[CH3:3].CC(C)=O.OS(O)(=O)=O.O=[Cr](=O)=O>CC(C)=O>[CH3:4][C:2]([NH:5][S:6]([C:9]1[S:17][C:16]2[S:15](=[O:19])(=[O:18])[N:14]([CH2:20][CH2:21][CH2:22][CH2:23][O:24][CH3:25])[CH2:13][C:12](=[O:26])[C:11]=2[CH:10]=1)(=[O:8])=[O:7])([CH3:1])[CH3:3]

Participants

4

Reactant 2

HCID 22901975HCID 22901975, compoundHCID 131709961Jones' reagent

Product 1

HCID 22902007HCID 22902007, compoundYield 80.3%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a solution of the product from Step A (9.5 g, 0.022 mol) in acetone (20 mL) at -10° C. was added freshly prepared Jones reagent (10 mL) and the mixture was stirred at room temperature for 2 hr. The solvent was evaporated and saturated aqueous sodium bicarbonate was added until the pH of the solution was 6. The aqueous mixture was extracted with ethyl acetate (4×50 mL). The combined extracts were washed with brine (2×10 mL), dried (MgSO4) and evaporated to provide a yellow solid (7.5 g, 78%).

Workup

  1. customThe solvent was evaporated
  2. additionsaturated aqueous sodium bicarbonate was added until the pH of the solution
  3. extractionThe aqueous mixture was extracted with ethyl acetate (4×50 mL)
  4. washThe combined extracts were washed with brine (2×10 mL)
  5. dry with materialdried (MgSO4)
  6. customevaporated

Sources & evidence

ORD record
ord-78d49e99ccf84590b95d52e2851b54cf
Source dataset
uspto-grants-1995_01
Patent number
US05378703

Reaction notes

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