Ethyl Acetate → HCID 10233537, compound

HRID 896681Notes

Reaction equation

HRID 896681 reaction equation
C(OC(=O)[C:5]1[CH:10]=[CH:9][C:8]([S:11][CH:12]([C:37]2[CH:42]=[CH:41][C:40]([S:43]([CH3:46])(=[O:45])=[O:44])=[CH:39][CH:38]=2)[CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([C:20]3[CH:21]=[C:22]([C:30]([S:33]([CH3:36])(=[O:35])=[O:34])([CH3:32])[CH3:31])[CH:23]=[C:24]4[C:29]=3[N:28]=[CH:27][CH:26]=[CH:25]4)[CH:15]=2)=[CH:7][CH:6]=1)C.[CH3:48][Mg]Br.C([O:54][CH2:55][CH3:56])(=O)C>C1COCC1.[Cl-].[NH4+]>[CH3:36][S:33]([C:30]([C:22]1[CH:23]=[C:24]2[C:29](=[C:20]([C:16]3[CH:15]=[C:14]([CH2:13][CH:12]([S:11][C:8]4[CH:7]=[CH:6][C:5]([C:55]([OH:54])([CH3:56])[CH3:48])=[CH:10][CH:9]=4)[C:37]4[CH:38]=[CH:39][C:40]([S:43]([CH3:46])(=[O:44])=[O:45])=[CH:41][CH:42]=4)[CH:19]=[CH:18][CH:17]=3)[CH:21]=1)[N:28]=[CH:27][CH:26]=[CH:25]2)([CH3:32])[CH3:31])(=[O:34])=[O:35]

Participants

6

Reactant 3

HCID 8857Ethyl AcetateHCID 10122718HCID 10122718, compoundHCID 178418573HCID 178418573, compound

Product 1

HCID 10233537HCID 10233537, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 25517Ammonium ChlorideSolvent

Conditions

Temperature
-78 °C

Procedure

A solution of Example 40 (280 mg, 0.4 mmol) and anhydrous CeCl3 (150 mg, 0,5 mmol) in THF (5 mL) was stirred at 21° C. for 1 h, then cooled at −78° C. Methylmagnesium bromide (3M, Ether, 0.6 mL, 2.1 mmol) was added and the resulting reaction mixture warmed slowly to 0° C., 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 hexane/ethyl acetate, 1:1 to 2:8) provided the title compound as a solid.

Workup

  1. customthe resulting reaction mixture
  2. temperaturewarmed slowly to 0° C.
  3. washThe organic extracts were washed (H2O), (brine),
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customPurification
  8. washby flash chromatography (eluting with hexane/ethyl acetate, 1:1 to 2:8)

Sources & evidence

ORD record
ord-5e7e4f377ae94d5d8668b8d8dd789cd5
Source dataset
uspto-grants-2005_07
Patent number
US06919353B2

Reaction notes

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