Methyl iodide → HCID 10164037, compound

HRID 896697Notes

Reaction equation

[CH3:1][O:2][C:3](=[O:35])[CH:4]([C:16]1[CH:21]=[CH:20][CH:19]=[C:18]([C:22]2[CH:23]=[C:24]([CH:32]([CH3:34])[CH3:33])[CH:25]=[C:26]3[C:31]=2[N:30]=[CH:29][CH:28]=[CH:27]3)[CH:17]=1)[CH2:5][C:6]1[CH:11]=[CH:10][C:9]([S:12]([CH3:15])(=[O:14])=[O:13])=[CH:8][CH:7]=1.[CH3:36]C(C)([O-])C.[K+].CI>C1COCC1.CN(C=O)C.[Cl-].[NH4+].C(OCC)(=O)C>[CH3:1][O:2][C:3](=[O:35])[C:4]([C:16]1[CH:21]=[CH:20][CH:19]=[C:18]([C:22]2[CH:23]=[C:24]([CH:32]([CH3:33])[CH3:34])[CH:25]=[C:26]3[C:31]=2[N:30]=[CH:29][CH:28]=[CH:27]3)[CH:17]=1)([CH3:36])[CH2:5][C:6]1[CH:11]=[CH:10][C:9]([S:12]([CH3:15])(=[O:14])=[O:13])=[CH:8][CH:7]=1

Participants

Conditions

Temperature: 21 °C

Procedure

To a solution of Example 92 (90 mg, 0.185 mmol) in THF/DMF (1:1, 2 mL) at −78° C. was added potassium tert-butoxide (1M, 0.19 mL, 0.19 mmol) dropwise followed by MeI (0,014 mL, 0.22 mmol) after 15 min. The resulting reaction mixture was stirred 18 h at 21° 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, 50:50) provided the title compound.

Workup

customThe resulting reaction mixture
washThe organic extracts were washed (H2O, brine)
dry with materialdried (MgSO4)
filtrationfiltered
concentrationconcentrated
customPurification
washby flash chromatography (eluting with hexane/ethyl acetate, 50:50)

Sources & evidence

ORD record: ord-d23a1d754b4345edb59ab21af2cbc597
Source dataset: uspto-grants-2005_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06919353B2

Reaction notes

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