HCID 10282979, compound → HCID 10189879, compound

HRID 896677Notes

Reaction equation

HRID 896677 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:45])[C:9]([C:35]2[CH:40]=[CH:39][C:38]([S:41]([CH3:44])(=[O:43])=[O:42])=[CH:37][CH:36]=2)([CH3:34])[CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([C:17]3[CH:18]=[C:19]([C:27]([S:30]([CH3:33])(=[O:32])=[O:31])([CH3:29])[CH3:28])[CH:20]=[C:21]4[C:26]=3[N:25]=[CH:24][CH:23]=[CH:22]4)[CH:12]=2)=[CH:4][CH:3]=1.[CH3:46][Mg]I>C(Cl)Cl.[Cl-].[NH4+].C(OCC)(=O)C>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([OH:45])([C:9]([C:35]2[CH:36]=[CH:37][C:38]([S:41]([CH3:44])(=[O:42])=[O:43])=[CH:39][CH:40]=2)([CH3:34])[CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([C:17]3[CH:18]=[C:19]([C:27]([S:30]([CH3:33])(=[O:31])=[O:32])([CH3:28])[CH3:29])[CH:20]=[C:21]4[C:26]=3[N:25]=[CH:24][CH:23]=[CH:22]4)[CH:12]=2)[CH3:46])=[CH:4][CH:3]=1

Participants

6

Reactant 2

HCID 10282979HCID 10282979, compoundHCID 178418373HCID 178418373, compound

Product 1

HCID 10189879HCID 10189879, compound

Reagents, catalysts & solvents 3

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolventHCID 25517Ammonium ChlorideSolvent

Conditions

Temperature
21 °C

Procedure

To a solution of Example 19 (93 mg, 0.144 mmol) in CH2Cl2 (4 mL) at −78° C. was added methyl magnesium iodide (3M, Et2O, 0.24 mL, 0.8 mmol) dropwise. The resulting reaction mixture was stirred at 21° C. for 12 h, then diluted with a saturated ammonium chloride solution and ethyl acetate. The organic extracts were washed (H2O), (brine), dried (MgSO4), filtered and concentrated. Purification by flash chromatography (eluting with dichloromethane/methanol, 99:1, 2×), then stirring vigorously the resulting residue in hexane/ethyl acetate/ether for 1 h and then filtration afforded the title compound as a white powder (mixture of diastereoisomers; 1:1).

Workup

  1. customThe resulting reaction mixture
  2. washThe organic extracts were washed (H2O), (brine),
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customPurification
  7. washby flash chromatography (eluting with dichloromethane/methanol, 99:1, 2×)
  8. stirringstirring vigorously the resulting residue in hexane/ethyl acetate/ether for 1 h
  9. filtrationfiltration

Sources & evidence

ORD record
ord-df2b004dc5f04e50a286cfecec83a0ab
Source dataset
uspto-grants-2005_07
Patent number
US06919353B2

Reaction notes

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