HCID 10229091, compound → HCID 10187078, compound

HRID 896676Notes

Reaction equation

HRID 896676 reaction equation
[CH3:1][S:2]([C:5]([C:8]1[CH:9]=[C:10]2[C:15](=[C:16]([C:18]3[CH:19]=[C:20]([CH2:24][CH:25]([C:28]4[CH:33]=[CH:32][C:31](SC)=[CH:30][CH:29]=4)CO)[CH:21]=[CH:22][CH:23]=3)[CH:17]=1)[N:14]=[CH:13][CH:12]=[CH:11]2)([CH3:7])[CH3:6])(=O)=[O:3].O[O:37][S:38]([O-:40])=O.[K+].[CH2:42]1COCC1.[CH3:47][OH:48].[OH2:49]>C(=O)(O)[O-].[Na+].C(OCC)(=O)C>[CH3:1][S:2]([C:5]([C:8]1[CH:9]=[C:10]2[C:15](=[C:16]([C:18]3[CH:19]=[C:20]([CH2:24][CH:25]([C:28]4[CH:29]=[CH:30][C:31]([S:38]([CH3:42])(=[O:40])=[O:37])=[CH:32][CH:33]=4)[CH2:47][OH:48])[CH:21]=[CH:22][CH:23]=3)[CH:17]=1)[N:14]=[CH:13][CH:12]=[CH:11]2)([CH3:7])[CH3:6])(=[O:3])=[O:49]

Participants

6

Reactant 3

HCID 10229091HCID 10229091, compoundHCID 21892291Methanol tetrahydrofuran waterHCID 23707502Potassium hydroxy sulfite

Product 1

HCID 10187078HCID 10187078, compound

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 516892Sodium BicarbonateSolvent

Conditions

Temperature
21 °C

Procedure

To a solution of Example 15 (350 mg, 0.69 mmol) in THF/MeOH/H2O (2:1:1, 15 mL) at 21° C. was added OXONE® (1.1 g, 1.8 mmol). The resulting reaction mixture was stirred 2 h at 21° C. then diluted with a sodium bicarbonate solution and ethyl acetate. The organic extracts were washed (H2O), (brine), dried (MgSO4), filtered and concentrated to afford the title compound as a pale yellow foam.

Workup

  1. customThe resulting reaction mixture
  2. washThe organic extracts were washed (H2O), (brine),
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-9c4d8a78cfc34251b6100cc78e821e4d
Source dataset
uspto-grants-2005_07
Patent number
US06919353B2

Reaction notes

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